Oxalyl chloride → tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate

HRID 2201969Notes

Reaction equation

HRID 2201969 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([O:11][C:12]([NH:14][C:15]1[S:16]C(C(O)=O)=[CH:18][N:19]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>ClCCl.O1CCCC1.CN(C)C=O>[C:7]([O:11][C:12](=[O:13])[NH:14][C:15]1[S:16][C:1]([C:2]([Cl:4])=[O:3])=[CH:18][N:19]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic Acid

Product 1

HCID 45117870tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The third step involves adding a 2M solution of oxalyl chloride in dichloromethane to a stirred solution of 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid in tetrahydrofuran and N,N-dimethylformamide, and then stirring the solution at room temperature for 4 hours. The solvent was evaporated under reduced pressure and in vacuo to obtain tert-butyl[5-(chlorocarbonyl)-1,3-thiazol-2-yl]carbamate.

Workup

  1. customThe solvent was evaporated under reduced pressure and in vacuo

Sources & evidence

ORD record
ord-faf669b11568465c9b53b18b4a5afecb
Source dataset
uspto-grants-2016_06
Patent number
US09365526B2

Reaction notes

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