Acetic Acid → HCID 58717821, compound

HRID 1245109Notes

Reaction equation

HRID 1245109 reaction equation
C[O:2][C:3](=[O:35])[C@@H:4]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[NH2:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:36]([C:40]1[CH:54]=[CH:53][C:43]([O:44][C:45]2[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=2)[CH:48]=O)=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:36]([C:40]1[CH:54]=[CH:53][C:43]([O:44][C:45]2[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=2)[CH2:48][NH:33][C:27]2[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=2[C:25]([NH:24][C@@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[CH:16][CH:17]=3)=[CH:10][CH:11]=2)[C:3]([OH:2])=[O:35])=[O:34])=[CH:42][CH:41]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 946533-(4-tert-Butylphenoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69609795(2S)-(2-Amino-5-chloro-benzoylamino)-3-(4'-cyclohexyl-biphenyl-4-yl)propionic acid methyl ester

Product 1

HCID 58717821HCID 58717821, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Reductive amination was carried out using (2S)-(2-amino-5-chloro-benzoylamino)-3-(4′-cyclohexyl-biphenyl-4-yl)propionic acid methyl ester (123 mg, 0.25 mmol), 3-(4-tert-butyl-phenoxy)-benzaldehyde (130 mg, 98%, 0.5 mmol), acetic acid (0.7 mmol), sodium triacetoxyborohydride (131 mg, 97%, 0.6 mmol) and DCE (2.5 mL). The mixture was stirred for 7 h. Purification by flash chromatography (ethyl acetate/hexanes 1:9) gave the title compound as colorless oil (139 mg, 0.19 mmol, 76% yield).

Workup

  1. customPurification by flash chromatography (ethyl acetate/hexanes 1:9)

Sources & evidence

ORD record
ord-6ef81e4412ac402fb35252eafd6d5bc9
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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