Lithium Hydroxide → (2E,4R)-5-(1,1'-Biphenyl)-4-yl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-methyl-2-pentenoic acid

HRID 1844797Notes

Reaction equation

HRID 1844797 reaction equation
C([O:3][C:4](=[O:30])/[C:5](/[CH3:29])=[CH:6]/[C@H:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C.[OH-].[Li+]>C(O)C>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:10][C:9]([CH2:8][C@@H:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])/[CH:6]=[C:5](\[CH3:29])/[C:4]([OH:30])=[O:3])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58027475LCZ-696 Impurity 22

Product 1

HCID 56846981(2E,4R)-5-(1,1'-Biphenyl)-4-yl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-methyl-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester (CAS#149709-59-1) is hydrolysed using lithium hydroxide in ethanol to yield (E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid as a white solid. δH (400 MHz; DMSO) 1.31 (9H, s, (CH3)3), 1.59 (3H, s, 1-CH3), 2.68 (1H, dd, J 6.8, 13.2, 5-HA), 2.86 (1H, m, 5-HB), 4.44 (1H, m, 4-H), 6.51 (1H, d, J 9.2, 3-H), 7.16 (1H, d, J 8.0, NH), 7.26 (2H, d, J 8.0, Ar-ortho-H(Ph)), 7.31 (1H, t, J 7.6, Ar-(Ph)-para-H), 7.40 (2H, t, J 8.0, Ar-(Ph)-meta-H), 7.54 (2H, d, J 8.0, Ar-meta-H(Ph), 7.60 (2H, d, J 7.6, Ar-(Ph)-ortho-H), 12.26 (1H, s, CO2H); m/z (+ESI) 404 ([MNa]+, 17%), 382 ([MH]+, 2), 326 (10), 264 (100), 167 (13).

Sources & evidence

ORD record
ord-4d75de8fb75145269ad3659e7a0149bd
Source dataset
uspto-grants-2015_02
Patent number
US08946481B2

Reaction notes

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