Sodium Methoxide → (2r,4s)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid sodium salt

HRID 1477427Notes

Reaction equation

HRID 1477427 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C@@H:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.C[O-].[Na+:31]>C(O)C>[Na+:31].[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:9][C@@H:10]([CH3:14])[C:11]([O-:13])=[O:12])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 46193546(2R,4S)-2-methyl-4-((2-methylpropan-2-yl)oxycarbonylamino)-5-(4-phenylphenyl)pentanoic acid

Product 1

HCID 66958285(2r,4s)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid sodium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (2R,4S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid (R1=Boc, R2=H, R3=CO2H) is added to ethanol (10 ml). Sodium methoxide (141 mg) is then added and the mixture is stirred at room temperature for 30 minutes. The mixture is then concentrated in vacuo to afford (2R,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid sodium salt (1-a, R1=Boc, R2=H, R3=CO2−Na+). 1H NMR (DMSO-d6): 0.91 (3H), 1.29 (1H), 1.34 (9H), 1.61 (1H), 2.12 (1H), 2.68-2.81 (2H), 3.60 (1H), 7.25-7.27 (2H), 7.32-7.36 (1H), 7.43-7.47 (2H), 7.55-7.57 (2H), 7.64-7.66 (2H), 7.76 (1H).

Workup

  1. concentrationThe mixture is then concentrated in vacuo

Sources & evidence

ORD record
ord-19ebf2e78ad14b8ebe904f655d86ce75
Source dataset
uspto-grants-2016_08
Patent number
US09403766B2

Reaction notes

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