Methanol → Methyl 3-Amino-2(S)-phenylsulfonylaminopropionate hydrochloride

HRID 583650Notes

Reaction equation

HRID 583650 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([OH:6])=[O:5].O=S(Cl)[Cl:19].[CH3:21]O>>[ClH:19].[NH2:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([O:6][CH3:21])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic Acid

Product 1

HCID 22865877Methyl 3-Amino-2(S)-phenylsulfonylaminopropionate hydrochloride

Procedure

To a stirred solution of 2-1b (5.0 g, 21 mmol) in CH3OH (100 mL) at 0° C. was added SOCl2 (7.5 mL, 100 mmol) dropwise. The cooling bath was then removed and the solution stirred at ambient temperature for 20 h. Concentration and trituration with ether gave 2-2 as a white solid.

Workup

  1. customThe cooling bath was then removed
  2. concentrationConcentration and trituration with ether

Sources & evidence

ORD record
ord-3971192fc39940f886d11dad2ca815a3
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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