Tetrahydrofuran → HCID 67343811, compound

HRID 1669488Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[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][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:39]([O:43][C:44]([N-:46][S:47](N1C=CC(=[N+](C)C)C=C1)(=[O:49])=[O:48])=[O:45])([CH3:42])([CH3:41])[CH3:40].[CH2:59]1COCC1>CCOC(C)=O>[C:39]([O:43][C:44]([N:46]([CH3:59])[S:47]([N:32]1[CH2:33][CH2:34][N:29]([CH2:28][CH2:27][CH2:26][CH:16]2[CH2:15][N:14]3[C:13]4[CH:12]=[C:11]([C:35]([O:37][CH3:38])=[O:36])[CH:10]=[CH:9][C:8]=4[C:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[C:21]3[C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[O:18][CH2:17]2)[CH2:30][CH2:31]1)(=[O:49])=[O:48])=[O:45])([CH3:42])([CH3:41])[CH3:40]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 14-cyclohexyl-7-(3-piperazin-1-ylpropyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.11 M) in dry THF was added (tert-butoxycarbonyl){[4-(dimethyliminio)pyridin-1(4H)-yl]sulfonyl}azanide (1 eq) (prepared following literature procedure: Winum, J.-Y. et al Org. Lett. 2001, 3, 2241-2243) and the mixture stirred at 40° C. for 2 h. The reaction was allowed to cool to RT before diluting with EtOAc. The combined organics were washed with 1N HCl (aq), sat. aq. NaHCO3 then brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product as a yellow foam (58%) that was used without further purification. (ES+) m/z 695 (M+H)+.

Workup

temperatureto cool to RT
washThe combined organics were washed with 1N HCl (aq), sat. aq. NaHCO3
dry with materialbrine, dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cfc53263109043a3aca365efd94759a3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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