2,2,2-Trifluoroethanol → HCID 69669549, compound

HRID 590763Notes

Reaction equation

HRID 590763 reaction equation
[CH2:1]([CH:4]1[C:8](=O)[CH2:7][CH:6]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5]1)[CH:2]=[CH2:3].[C:20]([O-:23])(=O)[CH3:21].[NH4+:24].[C:25]([N+:29]#[C-])([CH3:28])([CH3:27])[CH3:26].FC(F)(F)[CH2:33][OH:34]>C(Cl)Cl>[C:20]([NH:24][C@:8]1([C:33](=[O:34])[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:4]([CH2:1][CH:2]=[CH2:3])[CH2:5][C@H:6]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7]1)(=[O:23])[CH3:21]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 67513256HCID 67513256, compound

Product 1

HCID 69669549HCID 69669549, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl 2-(3-allyl-4-oxocyclopentyl)ethylcarbamate, mixture of isomers (0.50 g, 1.87 mmol) in 2,2,2-trifluoroethanol (2 mL) under nitrogen was treated with ammonium acetate (0.62 g, 8 mmol) and t-butylisonitrile (0.68 mL, 6.0 mmol) and stirred at room temperature for 3 days. The mixture was diluted with methylene chloride (20 mL) and added directly to a silica gel column (˜250 cc) and eluted with 1:1 ethyl acetate/heptane, then 2:1 ethyl acetate/heptane to afford tert-butyl 2-((1R,3S)-3-acetamido-4-allyl-3-(tert-butylcarbamoyl)cyclopentyl)ethylcarbamate (260 mg, 34%) as a white solid. NMR (CDCl3): δ 6.25 (br s, 1 H), 6.00 (br s, 1 H), 5.55-5.70 (m, 1 H), 4.90-5.00 (m, 2 H), 4.48 (m, 1 H), 3.03 (m, 2 H), 2.35-2.80 (m, 1 H), 2.27 (m, 1 H), 2.00-2.20 (m, 2 H), 1.70-2.00 (m, 2 H), 1.93 (s, 3 H), 1.45-1.65 (m, 4 H), 1.36 (s, 9 H), 1.27 (s, 9 H). MS (M+1): 410.3; MS (M+Na): 432.4.

Workup

  1. additionadded directly to a silica gel column (˜250 cc)
  2. washeluted with 1:1 ethyl acetate/heptane

Sources & evidence

ORD record
ord-5544010742964c2b8d21ac5287069261
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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