Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

HRID 900822Notes

Reaction equation

HRID 900822 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

Product 1

HCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[(tert-butoxycarbonyl)amino]thiazole-4-carboxylate (27.3 g, 100 mmol) prepared by the method of Kim and Kahn (Synlett, 1999, 8, 1239-1240) in 500 mL of THF at 0 C was added a solution of Red-A1 in toluene (80 mL of 65 wt % solution) dropwise. The reaction mixture was stirred for 1 d and then quenched with water and 1N HCl. Extracted 2×EtOAc and the EtOAc extracts were dried over MgSO4. The solution was filtered, concentrated by rotary evaporator, and chromatographed on SiO2 using 33% hexanes in EtOAC to give 20.5 g (89%) of 2-[(tert-butoxycarbonyl)amino]-4-hydroxymethylthiazole 42a. 1H-NMR (400 MHz, CDCl3): δ 6.98 (s, 1H), 4.81 (s, 2H), 1.81 (s, 9H).

Workup

  1. customquenched with water and 1N HCl
  2. extractionExtracted 2×EtOAc
  3. dry with materialthe EtOAc extracts were dried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated by rotary evaporator
  6. customchromatographed on SiO2 using 33% hexanes in EtOAC

Sources & evidence

ORD record
ord-f8114f46728c4040a3f81162af7488b6
Source dataset
uspto-grants-2008_04
Patent number
US07361654B2

Reaction notes

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