Acetic Acid → HCID 68862758, compound

HRID 1784246Notes

Reaction equation

HRID 1784246 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[NH2:34])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[CH3:37][O:38][C:39](=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:37][O:38][C:39](=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH:34][C:28]1[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:27]=1[C:26](=[O:35])[NH:25][C@H:4]([C:3]([O:2][CH3:1])=[O:36])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][CH:17]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81164Methyl 6-oxohexanoateHCID 5049666Sodium triacetoxyborohydrideHCID 68860943HCID 68860943, compound

Product 1

HCID 68862758HCID 68862758, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(S)-6-{4-Chloro-2-[1-methoxycarbonyl-2-(4′-phenoxy-biphenyl-4-yl)-ethylcarbamoyl]-phenylamino}-hexanoic acid methyl ester was prepared following Procedure G using (S)-2-(2-amino-5-chloro-benzoylamino)-3-(4′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (401 mg, 0.8 mmol), 6-oxo-hexanoic acid methyl ester (231 mg, 1.6 mmol), acetic acid (2.4 mmol), sodium triacetoxyborohydride (437 mg, 97%, 2 mmol) and DCE (6 mL). Purification by flash chromatography (ethyl acetate/hexanes 1:3) gave the title compound as yellow oil (418 mg).

Workup

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

Sources & evidence

ORD record
ord-d32bbcb522a34146bf012ecb64b58430
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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