2-Amino-5-chlorobenzoic acid → HCID 68860943, compound

HRID 1784245Notes

Reaction equation

HRID 1784245 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.[CH3:12][O:13][C:14](=[O:37])[C@@H:15]([NH2:36])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:12][O:13][C:14](=[O:37])[C@@H:15]([NH:36][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:2]=1[NH2:1])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[CH:21][CH:22]=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 68860407HCID 68860407, compound

Product 1

HCID 68860943HCID 68860943, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-(2-amino-5-chloro-benzoylamino)-3-(4′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester was prepared following Procedure A using 2-amino-5-chloro-benzoic acid (1.23 g, 7 mmol), (S)-2-amino-3-(4′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (2.43 g, 7 mmol), HBTU (3.19 g, 8.4 mmol) and DIEA (2.46 mL, 14 mmol) in DMF (35 mL). Purification by flash chromatography (ethyl acetate/hexanes 1:3, 1:2) gave the title compound as yellow solid (3.25 g, 6.49 mmol,).

Workup

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

Sources & evidence

ORD record
ord-a838c7ab372f470eb621f8cafa8982f4
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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