4-Methoxybenzenesulfonyl chloride → Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

HRID 1354074Notes

Reaction equation

HRID 1354074 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[CH:5]([CH2:7][OH:8])[NH2:6].CCN(CC)CC.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl.CN(C)C1C=CN=CC=1>[OH:8][CH2:7][CH:5]([NH:6][S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[C:4]([O:3][CH3:2])=[O:9]

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 517373Methyl DL-serinate hydrochloride

Product 1

HCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionateYield 97.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

DL-serine methylester HCl (14,6 g, 93,8 mmol) of the Chemical Formula 5 was suspended in 400 mL of dichloromethane, and Et3N (29 Ml, 206 mmol). and a catalytic amount of 4-dimethylaminopyridine were introduced therein while maintaining the temperature at 0° C., and 4-methoxybenzene-sulfonyl chloride (19.2 g 94 mmol) was add dropwise. They were stirred at room temperature for 20 hours, washed with 200 mL of distilled water, dried, and concentrated under reduced pressure to obtain a yellow solid title compound (26.5 g, yield 97%).

Workup

  1. washwashed with 200 mL of distilled water
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b162ea3b67924bf8ad37cd2ffcddf2ba
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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