Triethylamine → tert-butyl ((3S)-4-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-3-hydroxy-4-oxobutyl)carbamate
Reaction equation
S([O:5][CH2:6][CH2:7][N:8]1[C:12]([NH2:13])=[C:11]([NH2:14])[CH:10]=[N:9]1)(O)(=O)=O.[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][C@H:25]([OH:29])[C:26](O)=[O:27])=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>O>[NH2:13][C:12]1[N:8]([CH2:7][CH2:6][OH:5])[N:9]=[CH:10][C:11]=1[NH:14][C:26](=[O:27])[C@@H:25]([OH:29])[CH2:24][CH2:23][NH:22][C:20](=[O:21])[O:19][C:15]([CH3:16])([CH3:17])[CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol sulfate (2 g) and (2S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid (1.92 g) in water (8 ml) were added triethylamine (2.32 ml) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.76 g), and the mixture was stirred at room temperature for 3 hours. The whole mixture was extracted with ethyl acetate-tetrahydrofuran (1:1) and the solvent was evaporated under reduced pressure to give a crude product of tert-butyl ((3S)-4-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-3-hydroxy-4-oxobutyl)carbamate. The obtained crude product was used for Preparation 38 without further purification.
Workup
- extractionThe whole mixture was extracted with ethyl acetate-tetrahydrofuran (1:1)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-457df6e368d34b8cb523b4e61d867490
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192943B2
Reaction notes
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