Triethylamine → HCID 58641354, compound

HRID 1394950Notes

Reaction equation

HRID 1394950 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].[CH:14]1([C@H:17]([NH2:39])[C:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:19])[CH2:16][CH2:15]1.C(N(CC)CC)C>ClCCl>[CH:14]1([C@H:17]([NH:39][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:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:19])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 6102824HCID 6102824, compound

Product 1

HCID 58641354HCID 58641354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 4-nitrophenyl chloroformate (188 mg, 0.931 mmol, 1.10 equiv) in dichloromethane (5 mL) was added dropewise to a solution of (1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethanamine (16-7, 300 mg, 0.847 mmol, 1 equiv) and triethylamine (0.354 mL, 2.54 mmol, 3.00 equiv) in dichloromethane (10 mL) at 0° C. The reaction mixture was warmed to 23° C. and stirred for 20 hours. The reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL). The organic layer was washed with brine, then dried over magnesium sulfate and concentrated to provide 4-nitrophenyl(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethylcarbamate (31-1) as a pale yellow solid. LRMS m/z (M+H) 520.5 found, 520.2 required.

Workup

  1. customThe reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-56d87ddb267442b8bd403e8c631b8ec6
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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