Triethylamine → HCID 86597899, compound

HRID 459646Notes

Reaction equation

HRID 459646 reaction equation
[NH2:1][C@H:2]([C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:24])[C:22]=1[NH2:23])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][C:42](ON1C(=O)CCC1=O)=[O:43])=[O:38])([CH3:35])([CH3:34])[CH3:33]>C(Cl)(Cl)Cl>[NH2:23][C:22]1[N:21]([CH3:24])[N:20]=[CH:19][C:18]=1[NH:17][C:15](=[O:16])[C@@H:2]([NH:1][C:42](=[O:43])[CH2:41][CH2:40][NH:39][C:37]([O:36][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:38])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10684599Boc-Beta-Ala-OSuHCID 86597898HCID 86597898, compound

Product 1

HCID 86597899HCID 86597899, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl (5S)-5-amino-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-6-oxohexylcarbamate (1.60 g) and triethylamine (0.47 g) in chloroform (100 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (1.34 g). The mixture was stirred at room temperature for 15 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 (5S)-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-{[3-(tert-butoxycarbonylamino)propionyl]amino}-6-oxohexylcarbamate (2.09 g) 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-8584eb151e2445b59e4b6168d6f630cf
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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