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

HRID 1784242Notes

Reaction equation

HRID 1784242 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:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1.Cl>CCOC(C)=O>[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([NH:14][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([NH2:16])=[CH:18][CH:19]=1)[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 9784-Aminobenzoic AcidHCID 24720902(S)-Methyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride

Product 1

HCID 68861436(S)-2-(4-Amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl esterYield 21.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(4-Amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (415 mg) was prepared from (S)-2-amino-3-(4-bromo-phenyl)-propionic acid methyl ester-hydrochloride (1.5 g, 5.1 mmol) and 4-amino-benzoic acid (698 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 100 mL of EtOAc. The organic layer was washed with 1N HCl (2×), 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 (2×), 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-23962f4af22d4674b91c857de759d1cc
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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