Triethylamine → (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate

HRID 44636Notes

Reaction equation

HRID 44636 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].[O-]S([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[CH3:28][S:25]([O:1][CH2:2][C@@H:3]([NH:10][C:11]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24436Sodium SulfateHCID 31297Methanesulfonyl chlorideHCID 7016462(S)-2-((N-tert-Butoxycarbonyl)amino)-2-phenylethanol

Product 1

HCID 10335849(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The solution of 68.9 g (0.29 mol) of tert-butyl (1S)-2-hydroxy-1-phenylethylcarbamate and triethylamine (40.36 mL, 0.29 mol) in 700 mL of dry dichloromethane under inert atmosphere was cooled to −10° C. and 24.79 mL (0.319 mol) of mesylchloride were added dropwise. After 2 hours at 0° C. the mixture was poured into ice and water and extracted with dichloromethane. The organic phase was washed with diluted HCl, aqueous NaHCO3, brine and dried over Na2SO4 yielding 89.8 g of the product (98% yield).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with diluted HCl, aqueous NaHCO3, brine

Sources & evidence

ORD record
ord-13200e85ff694201877cc88e63376806
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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