Chloroform → HCID 86597891, compound

HRID 459637

Reaction equation

HRID 459637 reaction equation
[NH2:1][C@H:2]([C:14]([NH:16][C:17]1[CH:18]=[N:19][N:20]([CH3:42])[C:21]=1[NH:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[C:43]([O:47][C:48]([NH:50][CH2:51][C:52](ON1C(=O)CCC1=O)=[O:53])=[O:49])([CH3:46])([CH3:45])[CH3:44].C(Cl)(Cl)Cl>O1CCCC1>[C:43]([O:47][C:48]([NH:50][CH2:51][C:52]([NH:1][C@H:2]([C:14]([NH:16][C:17]1[CH:18]=[N:19][N:20]([CH3:42])[C:21]=1[NH:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:53])=[O:49])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 86597890HCID 86597890, compound

Product 1

HCID 86597891HCID 86597891, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (4S)-4-amino-5-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-5-oxopentylcarbamate (1.71 g) in tetrahydrofuran (30 ml) was added N-[2-(tert-butoxycarbonylamino)acetoxy]-succinimide (820 mg). The mixture was stirred at room temperature for 6 hours. To the reaction mixture was added chloroform (50 ml). The mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give tert-butyl (4S)-4-{[2-(tert-butoxycarbonylamino)acetyl]amino}-5-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-5-oxopentylcarbamate (2.1 g) as an oil.

Workup

  1. washThe mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26fc9a6986214205b8245fd54328da56
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Linked notes

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