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

HRID 47740노트

반응식

HRID 47740 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a919718f2197483cba02285fa4c0f945
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699895B2

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