Hydrochloric Acid → 3-Biphenyl-4-yl-(2S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester

HRID 2373839Notes

Reaction equation

HRID 2373839 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH2:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[Br:21][C:22]1[CH:23]=[CH:24][C:25]([OH:31])=[C:26]([CH:30]=1)[C:27](O)=[O:28].Cl>CCOC(C)=O>[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH:19][C:27](=[O:28])[C:26]1[CH:30]=[C:22]([Br:21])[CH:23]=[CH:24][C:25]=1[OH:31])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69725-Bromosalicylic acidHCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochloride

Product 1

HCID 692047733-Biphenyl-4-yl-(2S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl esterYield 27.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Biphenyl-4-yl-2-(S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (425 mg) was prepared from 2-(S)-amino-3-biphenyl-4-yl-propionic acid methyl ester-hydrochloride (1.0 g, 3.4 mmol), and 5-bromo-2-hydroxy-benzoic acid (744 mg, 3.4 mmol) as described in general procedure A except for an adapted work-up. After reaction completion, the reaction mixture was poured onto 150 mL of 1N HCl and 150 mL of EtOAc. The organic layer was washed with 1N HCl, saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The crude material was purified over silica gel (8:2, DCM-hexanes).

Workup

  1. customAfter reaction completion
  2. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude material was purified over silica gel (8:2, DCM-hexanes)

Sources & evidence

ORD record
ord-39610d4f542f46129789fc9ff8b2b693
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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