Hydrochloric Acid → HCID 67344671, compound

HRID 1669453Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][S:9]([N:12]([CH3:51])[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][O:21][C@H:22]1[CH2:29][N:28]2[C:30]3[CH:31]=[C:32]([C:43]([O:45]C)=[O:44])[CH:33]=[CH:34][C:35]=3[C:36]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[C:27]2[C:26]2[CH:47]=[CH:48][CH:49]=[CH:50][C:25]=2[O:24][CH2:23]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][S:9]([N:12]([CH3:51])[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][O:21][C@H:22]1[CH2:29][N:28]2[C:30]3[CH:31]=[C:32]([C:43]([OH:45])=[O:44])[CH:33]=[CH:34][C:35]=3[C:36]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[C:27]2[C:26]2[CH:47]=[CH:48][CH:49]=[CH:50][C:25]=2[O:24][CH2:23]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl (7S)-7-[(1-{2-[{[(tert-butoxycarbonyl)amino]sulfonyl}(methyl)amino]ethyl}pyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (7 mM) in MeOH was treated with 2 N NaOH (10 eq). The mixture was stirred at 60° C. for 3 h. MeOH was eliminated in vacuo, the residue was dissolved in EtOAc and neutralized by adding 6 N HCl. The aqueous was extracted with EtOAc and the organics combined, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product. The material was taken on without further purification. (ES+) m/z 711 (M+H)+.

Workup

extractionThe aqueous was extracted with EtOAc
washwashed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto afford the product
customThe material was taken on without further purification

Sources & evidence

ORD record: ord-272c2a1f063340a99c18cd6e951f137c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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