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

HRID 590676Notes

Reaction equation

HRID 590676 reaction equation
[Br:1][CH:2]1[CH2:23][CH2:22][C:5]2=[CH:6][C:7]3[C:8]4[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][C:9]=4[CH2:10][O:11][C:12]=3[CH:13]=[C:4]2[C:3]1=[O:24].[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([OH:41])=[O:40])=[O:32])=[O:28].C([O-])([O-])=O.[K+].[K+]>ClCCl>[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([O:41][CH2:19][C:18]([C:15]1[CH:16]=[CH:17][C:8]2[C:7]3[CH:6]=[C:5]4[CH2:22][CH2:23][CH:2]([Br:1])[C:3](=[O:24])[C:4]4=[CH:13][C:12]=3[O:11][CH2:10][C:9]=2[CH:14]=1)=[O:21])=[O:40])=[O:32])=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866883729-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-oneHCID 86723610(2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid

Product 1

HCID 86723609(2S,5S)-2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (4.00 g, 8.88 mmol) in dichloromethane (50 mL) was added (2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid (2.80 g, 9.32 mmol) and K2CO3 (1.84 g, 13.31 mmol). The resulting slurry was stirred at room temperature for 18 h. The reaction was diluted with dichloromethane and washed with aqueous HCl (0.5 M) and Brine. The aqueous layers were back extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was taken directly into the next reaction.

Workup

  1. washwashed with aqueous HCl (0.5 M) and Brine
  2. extractionThe aqueous layers were back extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was taken directly into the next reaction

Sources & evidence

ORD record
ord-e20f73d7ea044d97840e7a0c327a4533
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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