Water → 14-cyclohexyl-7-{[2-(methylamino)ethoxy]methyl}-N-{[methyl(2-oxoethyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

HRID 1669496Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([NH:34][S:35]([N:38]([CH2:40][CH:41](OC)[O:42]C)[CH3:39])(=[O:37])=[O:36])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][O:27][CH2:28][CH2:29][NH:30][CH3:31])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([NH:34][S:35]([N:38]([CH3:39])[CH2:40][CH:41]=[O:42])(=[O:36])=[O:37])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][O:27][CH2:28][CH2:29][NH:30][CH3:31])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of (7R or 7S)-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7-{[2-(methylamino)ethoxy]methyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide (0.05 M) in DCM was treated with an excess of TFA and H2O (>50 eq of each). The mixture was stirred at 40° C. for 40 min. The solution was allowed to cool to RT and used in the next step. (ES+) m/z 597 (M+H)+.

Workup

temperatureto cool to RT

Sources & evidence

ORD record: ord-843531ba282c4323b8a587514d11bc11
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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