Sodium borohydride → tert-Butyl (4-(2-hydroxyethyl)thiazol-2-yl)carbamate

HRID 1430637Notes

Reaction equation

HRID 1430637 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[S:9][CH:10]=1)C.[BH4-].[Na+]>CCO>[C:15]([O:14][C:12](=[O:13])[NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][CH2:4][OH:3])[N:7]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13240238HCID 13240238, compound

Product 1

HCID 22405510tert-Butyl (4-(2-hydroxyethyl)thiazol-2-yl)carbamateYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2-tert-Butoxycarbonylamino-thiazol-4-yl)-acetic acid ethyl ester (4 g, 13.9 mmol) in EtOH (50 ml), NaBH4 (1.59 g, 41.9 mmol) was added at 0° C. and stirred at r.t. for 18 h. Solvent was removed under reduced pressure and extracted in Ethyl acetate (150 ml) washed with brine (2×30 ml) dried over Na2SO4. After evaporation, the residue was purified by preparative chromatography (1:3 EtOAc:Hexanes) to give [4-(2-Hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (2.2 g, 65%). 1H NMR (400 MHz, CDCl3): 1.): 1.53 (s, 9H), 2.87 (t, J=5.2 2H), 3.90 (t, J=5.2 Hz, 2H), 6.55 (s, 1H). MS (EI) m/z: 245 (M+1).

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionextracted in Ethyl acetate (150 ml)
  3. washwashed with brine (2×30 ml)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation
  6. customthe residue was purified by preparative chromatography (1:3 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-5b0617816e344ee0bc419ff4bf4d6038
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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