Triethylamine → HCID 86597893, compound

HRID 459641Notes

Reaction equation

HRID 459641 reaction equation
[NH2:1][C@H:2]([C:14]([NH:16][C:17]1[CH:18]=[N:19][N:20]([CH3:23])[C:21]=1[NH2:22])=[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(N(CC)CC)C.[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][C:41](ON1C(=O)CCC1=O)=[O:42])=[O:37])([CH3:34])([CH3:33])[CH3:32]>C(Cl)(Cl)Cl>[NH2:22][C:21]1[N:20]([CH3:23])[N:19]=[CH:18][C:17]=1[NH:16][C:14](=[O:15])[C@@H:2]([NH:1][C:41](=[O:42])[CH2:40][CH2:39][NH:38][C:36]([O:35][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:37])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10684599Boc-Beta-Ala-OSuHCID 86597892HCID 86597892, compound

Product 1

HCID 86597893HCID 86597893, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl (4S)-4-amino-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-oxopentylcarbamate (4.90 g) and triethylamine (1.52 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (4.26 g). The mixture was stirred at room temperature for 17 hours. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of tert-butyl (4S)-5-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-4-{[3-(tert-butoxycarbonylamino)propionyl]amino}-5-oxopentylcarbamate as an oil. The crude product was used directly in the next step without further purification.

Workup

  1. washThe mixture was washed with 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-b9784bd6f3144fc0b2dc164b8906c9bc
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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