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

HRID 1669408Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:31]([NH:33][S:34]([N:37]([CH2:39][CH:40](OC)[O:41]C)[CH3:38])(=[O:36])=[O:35])=[O:32])=[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][C@@H:16]([O:26][CH2:27][CH2:28][NH:29][CH3:30])[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:31]([NH:33][S:34]([N:37]([CH3:38])[CH2:39][CH:40]=[O:41])(=[O:35])=[O:36])=[O:32])=[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][C@@H:16]([O:26][CH2:27][CH2:28][NH:29][CH3:30])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of (7S)-14-cyclohexyl-N-{[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}-7-[2-(methylamino)ethoxy]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide (0.06 M) in DCM was treated with an excess of TFA and H2O (>50 eq). The mixture was stirred at 40° C. for 30 min. All the volatiles were concentrated in vacuo to give the title compound, which was taken on without further purification. (ES+) m/z 583 (M+H)+.

Workup

concentrationAll the volatiles were concentrated in vacuo

Sources & evidence

ORD record: ord-c340688c50964058aa5e7e97494bfbbf
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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