Ethanol → ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)carbothioyl]amino}hexanoate
Reaction equation
[NH2:1][C@H:2]([CH2:18][OH:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:20]([N:24]=[C:25]=[S:26])([CH3:23])([CH3:22])[CH3:21].[N-]=C=S.[CH2:30]([OH:32])[CH3:31]>>[CH2:10]([O:9][C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([NH:1][C:25]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[S:26])[C:18]([O:32][CH2:30][CH3:31])=[O:19])=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
The process is performed as in Example 9, starting with 0.42 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate and 0.24 cm3 of tert-butyl isothiocyanate in 30 cm3 of ethanol at a temperature in the region of 20° C. for 3 days. The reaction is completed by addition of a further 0.48 cm3 of isothiocyanate followed by heating for 1 hour at a temperature in the region of 80° C. After an identical work-up, 0.6 g of ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)-carbothioyl]amino}hexanoate is obtained in the form of a beige-colored oil with a tendency to crystallize. (Rf=0.62 in a 90/10 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).
Sources & evidence
- ORD record
- ord-6e2f2ce12ca4468888b7e24fa402b795
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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