Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[CH3:36][NH:37][O:38][CH3:39].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:37]([O:38][CH3:39])[CH3:36])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (14 g, 0.0573 mol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (10.06 g, 0.0573 mol) and N-methyl morpholine (5.79 g, 0.0573 mol) in tetrahydrofuran was stirred for 2 hours at room temperature. N,O-Dimethylhydroxylamine hydrochloride (5.59 g, 0.0573 mmol) and triethylamine (5.59 g, 0.0573 mol) were added and the mixture was stirred for 3 days. The reaction mixture was evaporated and ethyl acetate was added. The reaction mixture was washed with 1 N aqueous hydrochloric acid and then washed with saturated aqueous sodium bicarbonate. [4-(Methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (14.5 g, 88%) was obtained as a tan tar after drying (magnesium sulfate) and evaporation.
Workup
- customThe reaction mixture was evaporated
- additionethyl acetate was added
- washThe reaction mixture was washed with 1 N aqueous hydrochloric acid
- washwashed with saturated aqueous sodium bicarbonate
Sources & evidence
- ORD record
- ord-59be9c7ae1d246e5bf7b527b4f99c272
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427635B2
Linked notes
Loading…