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

HRID 47740ノート

反応式

HRID 47740 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a919718f2197483cba02285fa4c0f945
出典データセット
uspto-grants-2004_03
特許番号
US06699895B2

反応ノート

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