Hydrogen chloride-ethyl acetate → Hydrochloric Acid

HRID 58803Notes

Reaction equation

HRID 58803 reaction equation
C(OC([NH:8][C@@H:9]([CH3:33])[C:10]([NH:12][C@@H:13]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11])=O)(C)(C)C.[ClH:34].CCOC(C)=O>>[NH2:8][C@@H:9]([CH3:33])[C:10]([NH:12][C@@H:13]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11].[ClH:34]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59254431(S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate

Product 2

HCID 313Hydrochloric AcidHCID 130394596(S)-benzyl 2-((S)-2-aminopropanamido)-3-(4-methoxyphenyl)propanoate

Procedure

A solution of (S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate (29.0 g, 63.6 mmol) in 3 N HCl-EtOAc (150 mL) was stirred for 1 h at ambient temperature. The mixture was concentrated and the residue was washed with petroleum ether (100 mL) to afford (S)-benzyl 2-((S)-2-aminopropanamido)-3-(4-methoxyphenyl)propanoate as an HCl salt (quant.), which was used directly in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residue was washed with petroleum ether (100 mL)

Sources & evidence

ORD record
ord-994c34d7db0c4a69bbdac155e930d8e8
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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