Hydrochloric Acid → HCID 69204773, compound

HRID 1245072Notes

Reaction equation

HRID 1245072 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 69204773HCID 69204773, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Biphenyl-4-yl-(2S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (2.75 g, 35%) was prepared from (2S)-amino-3-biphenyl-4-yl-propionic acid methyl ester-hydrochloride (5.0 g, 17.2 mmol), 5-bromo-2-hydroxy-benzoic acid (3.7 g, 17.2 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 (7:3, 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 (7:3, DCM-hexanes)

Sources & evidence

ORD record
ord-8f647a6c956b4477bf41507894addb56
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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