Triethylamine → [1-(4-Carbamoyl-oxazol-2-yl)-cyclopropyl]-carbamic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[O:16][CH:17]=[C:18]([C:20]([OH:22])=O)[N:19]=2)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:24](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C(=O)([O-])O.[NH4+]>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1([C:15]2[O:16][CH:17]=[C:18]([C:20](=[O:22])[NH2:24])[N:19]=2)[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-(1-benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid (0.20 g, 0.66 mmol) in DMF (3 mL) was added HATU (0.25 g, 0.66 mmol) and Et3N (0.16 g, 2.0 mmol). Ammonium hydrogen carbonate was then added and the reaction vessel sealed. The mixture was heated at 60° C. for 18 h. The reaction was allowed to cool to room temperature and diluted with water. The mixture was extracted with EtOAc (3×100 mL) and the combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give [1-(4-carbamoyl-oxazol-2-yl)-cyclopropyl]-carbamic acid benzyl ester (0.17 g, 0.55 mmol).
Workup
- customthe reaction vessel sealed
- temperatureto cool to room temperature
- extractionThe mixture was extracted with EtOAc (3×100 mL)
- washthe combined extracts were washed with water, brine
- dry with materialdried with MgSO4
- filtrationThe mixture was filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ac6b32f5d4d64647a0dc58f28d4735ca
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552205B2
Reaction notes
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