Trifluoroacetic acid → HCID 58551369, compound
Reaction equation
[CH3:1][S:2]([C:5]1[N:13]2[C:8]([C:9]3([CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=32)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][S:2]([C:5]1[N:13]2[C:8]([C:9]3([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=32)=[CH:7][CH:6]=1)(=[O:4])=[O:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of tert-butyl 1′-methylsulfonylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (200 mg, 0.48 mmol) in dry dichloromethane (1 mL) at 0° C. was added TFA (147 μL, 1.91 mmol). The cooling bath was removed and the mixture was stirred for 1.5 h at 25° C. The mixture was concentrated under reduced pressure and the residue obtained was taken up in dichloromethane (10 ml) and was washed with aqueous saturated NaHCO3 (5 ml). The aqueous phase was extracted twice with dichloromethane (2×10 ml) and the organic phases were combined, dried, filtered and concentrated to yield 1′-methylsulfonylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine] as a light yellow foamy solid (150 mg, 99%). ESI-MS m/z calc. 318.1, found 319.3 (M+1)+; Retention time 0.93 minutes (3 min run).
Workup
- customThe cooling bath was removed
- concentrationThe mixture was concentrated under reduced pressure
- customthe residue obtained
- washwas washed with aqueous saturated NaHCO3 (5 ml)
- extractionThe aqueous phase was extracted twice with dichloromethane (2×10 ml)
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-90bd11962e29486394fc95b6f1ef36c5
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365588B2
Reaction notes
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