Water → HCID 178461374, compound

HRID 531952Notes

Reaction equation

HRID 531952 reaction equation
[CH:1]1([N:7]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]=[O:17])=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>CO>[CH:1]1([N:7]([C@H:18]2[CH2:19][CH2:20][C@H:21]([CH3:24])[CH2:22][CH2:23]2)[C:8]([NH:10][C:11]2[S:12][C:13]([CH2:16][OH:17])=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 178461373HCID 178461373, compound

Product 1

HCID 178461374HCID 178461374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-cyclohexyl-3-(5-formyl-thiazol-2-yl)-1-(trans-4-methyl-cyclohexyl)-urea (175 mg, 0.5 mmol) in MeOH (5 mL) was added sodium borohydride (38 mg, 1 mmol). The mixture was stirred at rt for 10 min and the solution was poured into water (25 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layer was washed with water (2×20 mL), brine (1×20 mL), dried (anhydrous Na2SO4) and concentrated to get trans-1-cyclohexyl-3-(5-hydroxymethyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-urea in (90%, 158 mg) yield.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with water (2×20 mL), brine (1×20 mL)
  3. dry with materialdried (anhydrous Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fda5cea6886d4ba5b345308c99cb24d5
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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