Trifluoroacetic acid → HCID 131716454, compound
Reaction equation
C(OC([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([O:14][CH2:15][C:16]([O:18]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:17])[C:10]1=[O:32])=O)(C)(C)C.C1(OC)C=CC=CC=1.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[NH2:8][C@H:9]1[CH:12]([CH3:13])[N:11]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:10]1=[O:32]Participants
Procedure
(3S-trans)-[[3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinyl]oxy]acetic acid. diphenylmethyl ester (4.4 g1 10.0 mmol) was dissolved in a solution of 33 ml of trifluoroacetic acid and anisole (3.3 ml; 30.0 mmol) at -10° C. The mixture was evaporated in vacuo 10 minutes later and the residue was stirred with ether, filtered off and dried over P2O5 to give colorless crystals of (3S)-[[3-amino-4-methyl-2-oxo-1-azetidinyl]oxy]acetic acid, trifluoroacetate salt (yield 2.87 g). The salt (2.87 g; 10.0 mmol) was suspended in dry acetonitrile. MSTFA (5.57 ml; 30.0 mmol) was added and stirring was continued for 30 minutes. After evaporating in vacuo the residue was dissolved in dry tetrahydrofuran and then added to a mixture of the [[[(4-methoxyphenyl)methoxy]-carbonyl]amino]benzeneacetic acid 1-hydroxybenzotriazole ester (4. g, 10.0 mmol) in 25 ml of dry tetrahydrofuran at 0° C., stirred overnight at room temperature and evaporated in vacuo. After adding ether the crude silylated product was decomposed with 1 ml methanol. After removing the solvents in vacuo the residue was stirred with ether/petroleum ether to give colorless crystals of the title compound.
Workup
- customThe mixture was evaporated in vacuo 10 minutes later
- filtrationfiltered off
- dry with materialdried over P2O5
Sources & evidence
- ORD record
- ord-97d3dfaaadbb4398918d50ab91c8cfec
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04939253
Reaction notes
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