Benzyl chloroformate → Ethyl-2-benzyloxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

HRID 9092

Reaction equation

HRID 9092 reaction equation
[C:1]([O-:4])([OH:3])=[O:2].[Na+].[CH2:6]([O:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[CH3:7].ClC(O[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O>C1COCC1.ClCCl.O>[CH2:6]([O:8][C:9]([C:11]1[S:15][C:14]([NH:16][O:2][C:1]([O:4][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:3])=[N:13][C:12]=1[CH3:17])=[O:10])[CH3:7]

Participants

7

Reactant 3

HCID 10387Benzyl chloroformate2×HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 21911467Ethyl-2-benzyloxycarbonyloxyamino-4-methyl-thiazole-5-carboxylateYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 3 M aq. NaHCO3 solution (10 mL, 30 mmol) was added to a stirred solution of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (372 mg, 2 mmol) in THF (20 mL) at 0–5° C. Benzyl chloroformate (500 μL) was added. After 2 h, additional benzyl chloroformate (500 μL) and the biphasic solution was stirred for an additional 2 h at 0–5° C. The mixture was diluted with dichloromethane (50 mL) and water (30 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated. The residue was chromatographed on a silica gel column. Elution with 10% EtOAc in hexanes followed by 20% and 30% EtOAc in hexanes afforded the title compound (310 mg, 48%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column
  6. washElution with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-f75c4e99532d4a508cd22f8965bec48f
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Linked notes

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