Chlorosuccinimide → HCID 67242260, compound

HRID 2423163Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[C:22]4[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28][O:27][C:23]4=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[Cl:1][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]3[O:27][CH2:28][CH2:29][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][C:22]3=2)[N:18]([S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH:19]=1

Participants

Conditions

Temperature: 130 °C

Procedure

N-chlorosuccinimide (0.23 g, 0.54 mmol) was added to a solution of tert-butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 17, 0.23 g, 0.54 mmol) in chloroform (4 mL) and heated at 130° C. for 40 minutes in a microwave heater. The mixture was evaporated and purified by flash chromatography on silica gel using MeOH and DCM (1:99) as the eluent to give 167 mg of tert-butyl 10-chloro-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate. This intermediate (167 mg, 0.360 mmol) was dissolved in EtOH (20 mL) and a solution of 10 M KOH (0.2 mL, 2 mmol) was added. The mixture was heated at 65° C. for 20 minutes and the reaction mixture was evaporated and purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN) to give an off-white solid (40 mg) in the form of the trifluoroacetate salt. MS m/z 223 [M+H−Boc]+.

Workup

customThe mixture was evaporated
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-0ab4e065c06b4455a25c20b2dab98a65
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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