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

HRID 1280645Notes

Reaction equation

HRID 1280645 reaction equation
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10]O)=[S:7])(C)(C)C.Cl>CO>[CH:13]1([CH2:12][C@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86584434N-(tert-butyl)-N'-[(1S)-1-cyclohexylmethyl-2-hydroxyethyl]thiourea

Product 1

HCID 69697481(-)-(4S)-4-cyclohexylmethyl-4,5-dihydro-1,3-thiazol-2-ylamineYield 44.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

The process is performed as in Example 1, starting with 11.1 g of N-(tert-butyl)-N′-[(1S)-1-cyclohexylmethyl-2-hydroxyethyl]thiourea in 110 cm3 of aqueous 6N hydrochloric acid maintained at a temperature in the region of 100° C. for 2 hours. By means of an identical work-up, 3.6 g of (−)-(4S)-4-cyclohexylmethyl-4,5-dihydro-1,3-thiazol-2-ylamine are obtained in the form of a white solid melting at 169° C. (αD20=−33.9±0.8 at a concentration of 0.5% in methanol).

Sources & evidence

ORD record
ord-c1d618c81b9a4953aa804f4e0d62e70a
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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