Diisopropylethylamine → (S)-4-(3-tert-butoxycarbonylmethyl-ureido)-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester

HRID 2384047Notes

Reaction equation

HRID 2384047 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CCN(C(C)C)C(C)C.[CH2:19]([O:21][C:22](=[O:44])[C@@H:23]([CH3:43])[CH2:24][CH:25]([N:40]=[C:41]=[O:42])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)=[CH:29][CH:28]=1)[CH3:20]>CN(C=O)C>[CH2:19]([O:21][C:22](=[O:44])[C@@H:23]([CH3:43])[CH2:24][CH:25]([NH:40][C:41]([NH:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:42])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)=[CH:29][CH:28]=1)[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 86648210(S)-5-(3'-Chloro-biphenyl-4-yl)-4-isocyanato-2-methyl-pentanoic acid ethyl ester

Product 1

HCID 67506149(S)-4-(3-tert-butoxycarbonylmethyl-ureido)-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Next, to a solution of tert-butyl 2-aminoacetate (140 mg, 1.065 mmol) in DMF (5 mL) is added DIEA (344 mg, 2.66 mmol). The solution is stirred at room temperature for 5 minutes then (S)-5-(3′-chloro-biphenyl-4-yl)-4-isocyanato-2-methyl-pentanoic acid ethyl ester (330 mg, 0.887 mmol) is added. The mixture is stirred at room temperature for 2 hours then the solvent is removed under reduced pressure to give (S)-4-(3-tert-butoxycarbonylmethyl-ureido)-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester which is used directly in the following reaction.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d74914d16d4a4454897bd4fb9a31c885
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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