Triethylamine → HCID 59656614, compound

HRID 2054761Notes

Reaction equation

HRID 2054761 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22]1[CH2:26][N:25]([C:27]([C@@H:29]([NH2:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:24]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:23]=1.C(N(CC)CC)C>C1COCC1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22]1[CH2:26][N:25]([C:27]([C@@H:29]([NH:34][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:24]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 24901496HCID 24901496, compound

Product 1

HCID 59656614HCID 59656614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-nitrophenyl chloroformate (300 mg, 1.49 mmol, 1.2 equiv) in THF (10 mL) was added drop wise to a stirred solution of (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-carbonyl}-2,2-dimethylpropylamine (6-1, 460 mg, 1.24 mmol, 1.0 equiv) and triethylamine (151 mg, 1.49 mmol, 1.2 equiv) in THF (10 mL) at 23° C. After 1 hr the reaction was filtered and the filtrate concentrated to a pale yellow gum which was purified by flash chromatography on silica gel. Elution with dichloromethane to 3% ethyl acetate/dichloromethane provided 2-hydroxyethyl (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylcarbamate (9-1) as a colorless foam LRMS m/z (M+H) 536.5 found, 535.2 required.

Workup

  1. filtrationAfter 1 hr the reaction was filtered
  2. concentrationthe filtrate concentrated to a pale yellow gum which
  3. customwas purified by flash chromatography on silica gel
  4. washElution with dichloromethane to 3% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-2932d3b8d9774653bd54a848a06f1a34
Source dataset
uspto-grants-2008_02
Patent number
US07329762B2

Reaction notes

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