Hydrochloric Acid → (-)-(4S)-4-(4-Aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride

HRID 1280639Notes

Reaction equation

HRID 1280639 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]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86584432ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)carbothioyl]amino}hexanoate

Product 1

HCID 69884709(-)-(4S)-4-(4-Aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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.

Workup

  1. customAfter concentration of the reaction medium under the same conditions, the foam obtained
  2. customthe phases are separated each time after settling
  3. filtrationThe resulting crystalline product is spin-filtered
  4. washwashed with hot acetonitrile
  5. customdried under reduced pressure (5 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-53ff484cad26483aa78335c6769b85e3
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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