Hydrochloric Acid → (-)-(4S)-4-(3-nitrobenzyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride
Reaction equation
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:22]>>[ClH:22].[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C@H:9]1[CH2:10][S:7][C:6]([NH2:5])=[N:8]1)([O-:21])=[O:20]Participants
Procedure
The process is performed as in Example 2, starting with N-(tert-butyl)-N′-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea in 80 cm3 of aqueous 6N hydrochloric acid. The heating time is 7 hours. The product is isolated in an identical manner and then purified by chromatography under an argon pressure of 80 kPa, on a column of silica gel (particle size 40-63μ; diameter 3.5 cm; height 30 cm), eluting with a dichloromethane/methanol mixture (95/5 by volume). The fractions corresponding to the expected product are collected. These fractions are combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 3.90 g of (−)-(4S)-4-(3-nitrobenzyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride are obtained in the form of a white solid melting at 220° C. (αD20=−18.4±0.05 at a concentration of 0.5% in methanol).
Workup
- customThe product is isolated in an identical manner
- custompurified by chromatography under an argon pressure of 80 kPa
- washon a column of silica gel (particle size 40-63μ; diameter 3.5 cm; height 30 cm), eluting with a dichloromethane/methanol mixture (95/5 by volume)
- customThe fractions corresponding to the expected product are collected
- concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
Sources & evidence
- ORD record
- ord-11dd7c537f084b7aa75b5631f1749c2c
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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