Acetic acid dissociates immediately in solution. Reaction A does not react further following the sample taken at the end of
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1 SUPPLEMENTAL Table S1. Assumptions made during fitting of the reaction model in Dynochem. ID Assumption A1 Acetic acid dissociates immediately in solution. A2 Reaction A does not react further following the sample taken at the end of the dedicated reaction time. A3 2 equivalents of acetic acid are consumed in reaction A. The methanesulfonic acid and amino alcohol neutralization occurs A instantaneously to form a salt upon amino alcohol addition (by setting the reaction rate constant to be several orders of magnitude higher than the other reactions occuring in the system). A5 The equilibrium between intermediates 5, 6, and 7 is aided by the H + ion. A6 It takes minutes to heat up from 20 C to the designated reaction temperature. A7 Reaction B is isothermal after the heat up to the designated reaction temperature. A8 The reaction to intermediate 5 is irreversible. A9 The actual composition of intermediates 5, 6, and 7 does not impact the
2 reaction and can be approximated as a single component. A10 Amino alcohol addition occurs immediately after cooldown to 20 C for all runs. A11 All reactions, with the exception of the dissociation of acetic acid, are irreversible. Equation S1. Calculation of overall mass concentration for each HPLC sample. = % Equation S2. Calculation of the moles of each component. = % Where: C overall = Overall mass concentration in system p = Number of system components Area% i = Normalized area% of component i RF i = Response factor of component i n i = Moles of component i
3 MW i = Molecular weight of component i m basis = Mass basis for reaction (grams of starting material) The molar quantities of each component can then be used in determining the reaction kinetics for the main reactions. calibration curve for product 3 HPLC Response (Peak Area) y = 23857x R² = Concentration (mg/ml) HPLC Response (Peak Area) calibration curve for diastereomer y = 23823x R² = Concentration (mg/ml) FigureS1. Calibration curve for product 3 and diasteroeomer. Response factors were obtained from each calibration by taking the inverse of the slope of the linear trends. The calculated response factors on LC s along with the molecular weights for each
4 major component are presented in Table S2. All other components in solution were assumed to be in small enough quantities that they would not have a significant impact on the moles calculated for each major component and no attempt was made to correct for this assumption. Table S2. Molecular weights and response factors for each major component. Compound LC1 Response Factor (RF) [(Conc. In mg/ml)/(peak Area)] LC2 Response Factor (RF) [(Conc. In mg/ml)/(peak Area)] E E E E-05.98E E E E-05.33E-05.19E-05 Diastereomer.1E-05.20E-05
5 Table S3. Full DoE Design Conditions and Data for End of Reaction B STD Run Block AcOH Equiv. Run Conditions Solvent MsOH Vol. Equiv. (ml/g) Reaction A Temp. ( C) Amino Alcohol Equiv. Reaction B Temp. ( C)
6 Material 1 (mol %) 2 (mol %) (mol %) Responses (mol %) (mol %) (mol %)
7 Table S. Full DoE Design Data for End of Reaction A STD Run Block AcOH Equiv. MsOH Equiv. Solvent Vol. (ml/g) Reaction A Temp. ( C) (mol %) 2 (mol %) (mol %) 9 (mol %)
8 Table S5. Full DoE Course Data for Reaction B STD
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22 Table S6. ANOVA for factorial model for diastereomer Source Sum of Mean df Squares Square F Value Prob > F Block Model < significant A-AcOH Equivalents < B-MsOH Equivalents C-Solvent Vol. (ml/g) E-Amino Alcohol
23 F-Reaction B Temp < BF Residual Lack of Fit significant Pure Error Cor Total Std. Dev R-Squared 0.97 Mean 3.69 Adj R-Squared C.V. % 5.11 Pred R- Squared 0.78 PRESS 2.03 Adeq Precision Final equation in terms of actual factors for formation of diastereomer : %= h
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