Triethylamine → 2-(N-t-Butoxycarbonylglycylamino)thiazolo[4,5-c]pyridine
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[C:11]([O:15][C:16]([NH:18][CH2:19][C:20](O)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.ClC(OCC(C)C)=O>CN(C=O)C.O>[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]([NH:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2-aminothiazolo[4,5-c]pyridine (530 mg, 3.5 mmole), 2.0 ml of N,O-bistrimethylsilylacetamide (BSA) and 7 ml of dimethylformamide was heated at 60° C. with stirring. The resulting clear solution was added to the chilled mixed anhydride solution which was prepared from N-t-butyloxycarbonyl glycine (700 mg, 4 mmoles), triethylamine (404 mg, 4 mmoles) and isobutyl chloroformate (546 mg, 4 mmoles) in 10 ml of dry DMF at -10° C. The reaction mixture was stirred 2 days at room temperature and then diluted with water and extracted with 450 ml of ethyl acetate. The extracts were combined, evaporated and triturated with chloroform to give 175 mg of the title compound. Additional product (155 mg) was obtained from the mother liquor. Total yield was 330 mg (30%), which was recrystallized from CH3OH. Mp. 204°~208° C. (dec.).
Workup
- additionThe resulting clear solution was added to the chilled
- stirringThe reaction mixture was stirred 2 days at room temperature
- extractionextracted with 450 ml of ethyl acetate
- customevaporated
- customtriturated with chloroform
Sources & evidence
- ORD record
- ord-8cd8baaebf8e42e3ab2323a28ce3d2b6
- Source dataset
- uspto-grants-1985_02
- Patent number
- US04500526
Reaction notes
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