Toluene → HCID 89595080, compound

HRID 1521693Notes

Reaction equation

HRID 1521693 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[NH:18][C:19]([CH3:38])([CH2:21][CH2:22][N:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:20].[C:39]([O:43][CH2:44]C)(=[O:42])[CH:40]=O.C1(C)C=CC=CC=1>CO>[CH3:44][O:43][C:39]([C:40]1[N:18]([C:19]([CH3:38])([CH2:21][CH2:22][N:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH3:20])[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:7])[CH:16]=[CH:17][C:2]=2[N:1]=1)=[O:42]

Participants

5

Reactant 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 67235406HCID 67235406, compound

Product 1

HCID 89595080HCID 89595080, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of crude benzyl 4-amino-3-({4-[bis(tert-butoxycarbonyl)amino]-2-methylbutan-2-yl}amino)benzoate (250 mg, 0.47 mmol) in methanol (10 mL) is added a 50% solution of ethyl glyoxalate in toluene (0.38 mL, 1.90 mmol). After 16 h, the solvent is evaporated to afford the title compound (295 mg, >99%), which is used in the next step without purification.

Workup

  1. customthe solvent is evaporated

Sources & evidence

ORD record
ord-bd826ae9eb6d48078593ff6999f3428b
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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