Diisopropylethylamine → (2r,4s)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid diisopropylethylammonium salt

HRID 588301Notes

Reaction equation

HRID 588301 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.[CH:29]([N:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH3:34])([CH3:31])[CH3:30]>C(O)C>[CH:29]([NH+:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH3:34])([CH3:31])[CH3:30].[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 81531DiisopropylethylamineHCID 46193546(2R,4S)-2-methyl-4-((2-methylpropan-2-yl)oxycarbonylamino)-5-(4-phenylphenyl)pentanoic acid

Product 1

HCID 131731041(2r,4s)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid diisopropylethylammonium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (2R,4S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid (1-a, R1=Boc, R2=H, R3=CO2H) is added to ethanol (10 ml). Diisopropylethylamine (0.454 ml) 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 diisopropylethylammonium salt (1-a, R1=Boc, R2=H, R3=CO2−[NHiPr2Et]+). 1H NMR (DMSO-d6): 0.95-0.98 (15H), 1.04 (3H), 1.32 (9H), 1.36 (1H), 1.74 (1H), 2.38-2.49 (3H), 2.67 (2H), 2.99 (2H), 3.66 (1H), 6.29 and 6.70 (1H), 7.23-7.25 (2H), 7.33-7.37 (1H), 7.42-7.46 (2H), 7.55-7.57 (2H), 7.62-7.64 (2H).

Workup

  1. concentrationThe mixture is then concentrated in vacuo

Sources & evidence

ORD record
ord-6d24a3308d8f4f74b56f1c0491768b84
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Reaction notes

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