Trifluoroacetic acid → HCID 121266575, compound
Reaction equation
[Br:1][C:2]1[CH:30]=[N:29][C:5]2[O:6][CH2:7][CH2:8][C@@H:9]3[C@@:14]([CH3:15])([C:4]=2[CH:3]=1)[N:13]=[C:12]([NH:16]C(=O)OC(C)(C)C)[C:11]1([CH2:26][CH2:25][CH2:24]1)[S:10]3(=[O:28])=[O:27].C(O)(C(F)(F)F)=O>>[NH2:16][C:12]1[C:11]2([CH2:26][CH2:25][CH2:24]2)[S:10](=[O:27])(=[O:28])[C@@H:9]2[CH2:8][CH2:7][O:6][C:5]3[N:29]=[CH:30][C:2]([Br:1])=[CH:3][C:4]=3[C@@:14]2([CH3:15])[N:13]=1Participants
Procedure
A flask was charged with tert-butyl ((4a′R,11b′R)-10′-bromo-11b′-methyl-4′,4′-dioxido-4a′,5′,6′,11b′-tetrahydrospiro[cyclobutane-1,3′-pyrido[3′,2′: 6,7]oxepino[4,5-b][1,4]thiazin]-2′-yl)carbamate (0.0306 g, 0.061 mmol) followed by the addition of TFA (1.0 ml, 13.46 mmol). The resulting mixture was stirred at rt for 15 min, quenched with water and the pH was brought to >10 using saturated NaHCO3 and 1 N NaOH, and extracted with DCM. The combined organics were dried over Na2SO4, filtered and concentrated to afford a white solid as (4a′R,11b′R)-2′-amino-10′-bromo-11b′-methyl-4a′,5′,6′,11b′-tetrahydrospiro[cyclobutane-1,3′-pyrido[3′,2′: 6,7]oxepino[4,5-b][1,4]thiazine]-4′,4′-dioxide (0.0192 g, 0.048 mmol, 78% yield). LC/MS (ESI) m/z=399.8 (M+H).
Workup
- customquenched with water
- extractionextracted with DCM
- dry with materialThe combined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3657a38d1cc24fb1ab3a158ec7ad2604
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309263B2
Reaction notes
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