Hydrochloric Acid → Methyl (2S)-3-amino-2-benzenesulfonamidopropanoate

Reaction equation

[C:1]1([S:7]([NH:10][C@@H:11]([CH2:16][NH:17]C(OC(C)(C)C)=O)[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CCOC(C)=O>[C:1]1([S:7]([NH:10][C@@H:11]([CH2:16][NH2:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 23-8 (0.35 g, 0.98 mmol) in EtOAc (5 mL) was cooled to -40° C. and saturated with HCl gas. The solution was warmed to 0° C. for 2 h, then concentrated to give 23-9 as a white solid.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-de48f4b301cf44efa04c36596a08d425
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416099

Reaction notes

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Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 10570372Methyl (S)-3-((tert-butoxycarbonyl)amino)-2-(phenylsulfonamido)propanoate

Product 1

HCID 10563154Methyl (2S)-3-amino-2-benzenesulfonamidopropanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent