Hydrochloric Acid → (+)-(4R)-4-(4-aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride

HRID 47729

反応式

HRID 47729 の反応式
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:25]O)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(=O)OCC1C=CC=CC=1)=[S:7])(C)(C)C.[ClH:27]>C(O)C>[ClH:27].[ClH:27].[NH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:25][S:7][C:6]([NH2:5])=[N:8]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86584427benzyl (5R)-5-{[(tert-butylamino)carbothioyl]amino}-6-hydroxyhexylcarbamate

生成物 1

HCID 69885654(+)-(4R)-4-(4-aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The process is performed as in Example 1, starting with 5.9 g of benzyl (5R)-5-{[(tert-butylamino)carbothioyl]amino}-6-hydroxyhexylcarbamate in 40 cm3 of aqueous 6N hydrochloric acid at a temperature in the region of 100° C. for 3 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 50° C., the residue obtained is taken up in ethanol and then concentrated again under the above conditions. The paste obtained is crystallized by trituration from an ethanol/methanol mixture (8/2 by volume). The crystals are filtered off, washed with acetonitrile and air-dried. 1.3 g of (+)-(4R)-4-(4-aminobutyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride are obtained in the form of a white solid melting at 188° C. (αD20=+16.2±0.7 at a concentration of 0.5% in methanol).

後処理

  1. customAfter concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 50° C., the residue obtained
  2. concentrationconcentrated again under the above conditions
  3. customThe paste obtained
  4. customis crystallized by trituration from an ethanol/methanol mixture (8/2 by volume)
  5. filtrationThe crystals are filtered off
  6. washwashed with acetonitrile
  7. customair-dried

出典と根拠

ORDレコード
ord-60932a1560cb45749a343713bab42d5f
出典データセット
uspto-grants-2004_03
特許番号
US06699895B2

関連ノート

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