Trifluoroacetic acid → HCID 18924896, compound

HRID 2209839Notes

Reaction equation

HRID 2209839 reaction equation
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:11][CH2:10][N:9]1C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([CH:8]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10002168HCID 10002168, compound

Product 1

HCID 18924896HCID 18924896, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.2 g (33.9 mmol) of N-(t-butyl)-4-(benzyloxycarbonyl)-1-(t-butyloxycarbonyl)piperazine-2-carboxamide in 100 ml of dichloromethane was treated with 20 ml of trifluoroacetic acid. The resulting solution was stirred at ambient temperature for 3 h, concentrated in vacuo, and treated with 800 ml of ethyl acetate. The solution was washed with 1 N NaOH. The aqueous layer was extracted with two portions of ethyl acetate, and the combined organic layers were washed with saturated brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using first 2% then 4% methanol in chloroform provided 8.42 g (78%) of the desired compound. 1H NMR (CDCl3)δ1.34 (s, 9H), 2.8 (m, 1H), 3.0 (m, 3H), 3.21 (dd, J=9, 4 Hz, 1H), 3.9 (m, 1H), 4.2 (m, 1H), 5.14 (AA', 2H), 6.6 (br, 1H), 7.3-7.4 (m, 5H). Mass spectrum: (M+H)+ =320.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with 800 ml of ethyl acetate
  3. washThe solution was washed with 1 N NaOH
  4. extractionThe aqueous layer was extracted with two portions of ethyl acetate
  5. washthe combined organic layers were washed with saturated brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c5a732531294a64af5ef4bf69b044ee
Source dataset
uspto-grants-1995_10
Patent number
US05455351

Reaction notes

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