2-Amino-5-chlorobenzoic acid → (2S)-(2-Amino-5-chloro-benzoylamino)-3-biphenyl-4-yl-propionic acid methyl ester

HRID 1245107Notes

Reaction equation

HRID 1245107 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([NH2:25])[CH2:17][C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1.CN(C(ON1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([NH:25][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:2]=1[NH2:1])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 124762-Amino-5-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24720902(S)-Methyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride

Product 1

HCID 69609659(2S)-(2-Amino-5-chloro-benzoylamino)-3-biphenyl-4-yl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-(2-Amino-5-chloro-benzoylamino)-3-biphenyl-4-yl-propionic acid methyl ester was prepared following General Procedure A using 2-amino-5-chloro-benzoic acid (1.751 g, 98%, 10 mmol), (S)-2-amino-3-(4-bromo-phenyl)-propionic acid methyl ester hydrochloride salt (2.95 g, 10 mmol), HBTU (4.55 g, 12 mmol) and DIEA (6.33 mL, 99%, 36 mmol) in DMF (60 mL). Purification by flash chromatography (ethyl acetate/hexanes 1:3, 1:2, 1:1.5) gave solid (3.48 g, 8.45 mmol, 85% yield).

Workup

  1. customPurification by flash chromatography (ethyl acetate/hexanes 1:3, 1:2, 1:1.5)

Sources & evidence

ORD record
ord-26ce3973a44349f6b229f3706f9a9c92
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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