2-Amino-5-chlorobenzoic acid → HCID 68866789, compound

HRID 1984814Notes

Reaction equation

HRID 1984814 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:31])[C@@H:15]([NH2:30])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[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:31])[C@@H:15]([NH:30][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][CH:26]=[C:25]([OH:29])[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 68871529HCID 68871529, compound

Product 1

HCID 68866789HCID 68866789, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-5-chloro-benzoic acid (1.95 g, 11.38 mmol) in DMF (10.0 mL) was reacted with (2S)-amino-3-(3′-hydroxy-biphenyl-4-yl)propionic acid methyl ester (3.50 g, 11.38 mmol), HBTU (3.98 g, 10.50 mmol), and DIEA (6.08 mL, 34.15 mmol) by the general procedure A. The crude product was purified by flash column chromatography on silical gel using DCM/hexane 85:15 and increasing the gradient to DCM and finally DCM containing 0.25% methanol, to give 1.75 g of (2S)-(2-amino-5-chloro-benzoylamino)-3-(3′-hydroxy-biphenyl-4-yl)propionic acid methyl ester as a white solid.

Workup

  1. customThe crude product was purified by flash column chromatography on silical gel
  2. temperatureincreasing the gradient to DCM and finally DCM containing 0.25% methanol

Sources & evidence

ORD record
ord-6df6825cb500459b90e29097cbfba39f
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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