Pyridiniumtribromide → (2S,5S)-2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

HRID 1751668Notes

Reaction equation

HRID 1751668 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:40]([CH3:42])[CH3:41])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17][CH2:18][C:19](=[O:39])[C:20]1[CH:21]=[CH:22][C:23]2[C:32]3[CH:31]=[C:30]4[CH2:33][CH2:34][CH2:35][C:36](=[O:37])[C:29]4=[CH:28][C:27]=3[O:26][CH2:25][C:24]=2[CH:38]=1)=[O:16])=[O:8])=[O:4].[Br-:43].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CO.Cl>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:40]([CH3:42])[CH3:41])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17][CH2:18][C:19]([C:20]1[CH:21]=[CH:22][C:23]2[C:32]3[CH:31]=[C:30]4[CH2:33][CH2:34][CH:35]([Br:43])[C:36](=[O:37])[C:29]4=[CH:28][C:27]=3[O:26][CH2:25][C:24]=2[CH:38]=1)=[O:39])=[O:16])=[O:8])=[O:4]

Participants

6

Reactant 2

HCID 21124087Pyridiniumtribromide2×HCID 69672293(2S,5S)-2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo [c,g]chromen-3-yl)ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Product 1

HCID 86688346(2S,5S)-2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2S,5S)-2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate (400 mg, 0.61 mmol) was dissolved in a solution of DCM (15 mL) and MeOH (6 mL), then treated with pyridinium tribromide (409 mg, 1.28 mmol). At 2 h, an additional portion of pyridinium tribromide (40 mg) was added. After stirring at RT for another 20 min, the reaction mixture was diluted with DCM and 10% HCl, and extracted with DCM. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure and the crude material was carried on without further purification.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was carried on without further purification

Sources & evidence

ORD record
ord-c98dbf91e568461197e91657039bc55f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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