Hydrochloric Acid → (-)-(4S)-4-(4-Aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride
Reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:22][C:23]([NH:25]C(C)(C)C)=[S:24])[C:17](OCC)=O)=O)C1C=CC=CC=1.[ClH:30]>C(OCC)C>[ClH:30].[ClH:30].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[CH2:17][S:24][C:23]([NH2:25])=[N:22]1Participants
Procedure
The process is performed as in Example 9, starting with 0.59 g of ethyl (2S)-6-{[(benzyloxy)-carbonyl]amino}-2-{[(tert-butylamino)carbothioyl]-amino}hexanoate in 6 cm3 of 6N hydrochloric acid. After concentration of the reaction medium under the same conditions, the foam obtained is taken up 3 times in diethyl ether and the phases are separated each time after settling has taken place, and the remaining insoluble material is then taken up in 10 cm3 of acetonitrile. The resulting crystalline product is spin-filtered, washed with hot acetonitrile and then dried under reduced pressure (5 kPa) at a temperature in the region of 20° C. 0.34 g of (−)-(4S)-4-(4-amino-butyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydro-chloride in the form of cream-colored crystals melting at 170° C. (αD20=−15.5±0.6 at a concentration of 0.5% in methanol).
Workup
- customAfter concentration of the reaction medium under the same conditions, the foam obtained
- customthe phases are separated each time after settling
- filtrationThe resulting crystalline product is spin-filtered
- washwashed with hot acetonitrile
- customdried under reduced pressure (5 kPa) at a temperature in the region of 20° C
Sources & evidence
- ORD record
- ord-a919718f2197483cba02285fa4c0f945
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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