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

HRID 1180553Notes

Reaction equation

HRID 1180553 reaction equation
[NH2:1][CH:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)Cl.C(N(CC)CC)C>[OH:4][CH2:3][CH:2]([NH:1][S:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1)(=[O:19])=[O:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 416960Methyl DL-serinate

Product 1

HCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionateYield 54%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of D,L-serine, methyl ester (5.0 g, 32.14 mmol) and triethylamine (15.7 ml, 0.012 mmol) in methylene chloride (100 ml), cooled to 0° C., was added, in portions, 4-methoxybenzenesulfonyl chloride (6.64 g, 32.14 mmol). The mixture was then stirred under argon at room temperature for 48 hours. The reaction was diluted with methylene chloride (100 ml), washed with water (60 ml), 2N citric acid (60 ml), saturated sodium chloride (60 ml), and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give a solid. Crystallization from ethyl acetate gave 5.0 g (54%) of the product as white crystals, mp 92-94° C.

Workup

  1. washwashed with water (60 ml), 2N citric acid (60 ml), saturated sodium chloride (60 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customto give a solid
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-903c8925165045aa8ebc3428c7d19fa9
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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