1-Octanethiol → 4-((S)-2-Amino-3-tert-butoxycarbonylamino-propionyl)-piperazine-1-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:41])[C@@H:13]([NH:23]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(S)CCCCCCC.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:41])[C@@H:13]([NH2:23])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.71 g 4-[(S)-3-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-piperazine-1-carboxylic acid ethyl ester in 50 ml THF was stirred in the presence of 4 ml 1-octanethiol and 90 μl DBU. After 12 h the mixture was concentrated, the residue dissolved in dichloromethane and extracted with 0.1 M HCl. The aqueous phase was brought to pH9 by adding aqueous NaHCO3 before being extracted with dichloromethane. The product was obtained after evaporation of the solvent and was used in the subsequent reaction.
Workup
- concentrationAfter 12 h the mixture was concentrated
- dissolutionthe residue dissolved in dichloromethane
- extractionextracted with 0.1 M HCl
- additionby adding aqueous NaHCO3
- extractionbefore being extracted with dichloromethane
- customThe product was obtained
- customafter evaporation of the solvent
- customwas used in the subsequent reaction
Sources & evidence
- ORD record
- ord-97e8c25b756843528e3e045e966e533d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426420B2
Reaction notes
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