Hydrochloric Acid → (S)-2-(5-Amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester

HRID 1784240Notes

Reaction equation

HRID 1784240 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([NH2:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:26])=[C:21]([CH:25]=1)[C:22](O)=[O:23].Cl>CCOC(C)=O>[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([NH:14][C:22](=[O:23])[C:21]1[CH:25]=[C:17]([NH2:16])[CH:18]=[CH:19][C:20]=1[Cl:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 378795-Amino-2-chlorobenzoic acidHCID 24720902(S)-Methyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride

Product 1

HCID 68861548(S)-2-(5-Amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl esterYield 15.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(5-Amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (316 mg) was prepared from (S)-2-Amino-3-(4-bromo-phenyl)-propionic acid methyl ester-hydrochloride (1.5 g, 5.1 mmol) and 5-amino-2-chloro-benzoic acid (909 mg, 5.1 mmol) as described in Procedure A, except for an adapted work-up. After reaction completion, the reaction mixture was poured onto 100 mL of 1N HCl and 50 mL of EtOAc. The organic layer was washed with 1N HCl, 10% sodium carbonate, dried over sodium sulfate and evaporated. The crude material was purified over silica gel (DCM-EtOAc, 9-1).

Workup

  1. customAfter reaction completion
  2. washThe organic layer was washed with 1N HCl, 10% sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude material was purified over silica gel (DCM-EtOAc, 9-1)

Sources & evidence

ORD record
ord-95f10ea146fa4dd798c4b19d25e814d7
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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