Hydrochloric Acid → HCID 69698838, compound

HRID 47737Notes

Reaction equation

HRID 47737 reaction equation
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:10](O)[CH3:11])=[S:7])(C)(C)C.Cl>O>[CH2:13]([C@H:9]1[C@H:10]([CH3:11])[S:7][C:6]([NH2:5])=[N:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86584431N-(tert-butyl)-N'-((1S)-1-benzyl-2-hydroxypropyl)thiourea

Product 1

HCID 69698838HCID 69698838, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The process is performed as in Example 3, starting with 3.9 g of diastereoisomer A of the N-(tert-butyl)-N′-((1S)-1-benzyl-2-hydroxypropyl)thiourea in 46 cm3 of aqueous 6N hydrochloric acid. After heating for 5 hours at a temperature in the region of 100° C., the reaction mass is concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. The oil obtained is dissolved in 50 cm3 of water; the solution is washed with twice 50 cm3 of dichloromethane. The aqueous phase is made alkaline by addition of 3 cm3 of 30% caustic soda and then extracted with 3 times 50 cm3 of dichloromethane. The organic extracts are combined and dried over sodium sulfate. After filtration and concentration under reduced pressure (5 kPa) at a temperature in the region of 40° C., 2.5 g of (−)-(4S,5S)-4-benzyl-5-methyl-4,5-dihydro-1,3-thiazol-2-ylamine are obtained in the form of a white solid melting at 89° C. (trans isomer). (αD20=−87.3±1.3 at a concentration of 0.5% in methanol).

Workup

  1. concentrationthe reaction mass is concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C
  2. customThe oil obtained
  3. washthe solution is washed with twice 50 cm3 of dichloromethane
  4. additionby addition of 3 cm3 of 30% caustic soda
  5. extractionextracted with 3 times 50 cm3 of dichloromethane
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration and concentration under reduced pressure (5 kPa) at a temperature in the region of 40° C., 2.5 g of (−)-(4S,5S)-4-benzyl-5-methyl-4,5-dihydro-1,3-thiazol-2-ylamine

Sources & evidence

ORD record
ord-8207a29a2ca34bfbb06ac18884f45932
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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