Dimethylamine → HCID 86617474, compound

HRID 1162818Notes

Reaction equation

HRID 1162818 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:9][CH:8]2[CH2:24][C:25]([OH:27])=O)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:48]([CH3:50])[CH3:49])C2C=CC=CC=2N=N1.CNC>C1COCC1.ClCCl>[CH3:49][N:48]([CH3:50])[C:25](=[O:27])[CH2:24][CH:8]1[CH2:9][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:11][C:12](=[O:13])[N:7]1[CH2:6][C:5]1[CH:28]=[CH:29][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68433380HCID 68433380, compound

Product 1

HCID 86617474HCID 86617474, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-(4-fluorobenzyl)-4-(benzyloxycarbonyl)-6-oxo-piperazin-2-yl]acetic acid (0.8 g, 2.0 mmol) in THF (30 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.07 g, 4.68 mmol) and dimethylamine (2.0 M in THF, 2.34 mL, 4.68 mmol). The reaction was stirred overnight. The reaction mixture was then diluted with dichloromethane, washed with aqueous hydrochloric acid, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography with silica gel using hexanes and ethyl acetate as eluents to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.23-7.38 (m, 7H), 7.01 (t, J=8.6 Hz, 2H), 5.0-5.24 (m, 3H), 4.45-4.60 (m, 1H), 3.88-4.26 (m, 4H), 3.02-3.20 (m, 1H), 2.62-2.95 (m, 6H), 2.42-2.62 (m, 1H), 2.24 (d, J=15.8 Hz, 1H).

Workup

  1. washwashed with aqueous hydrochloric acid, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography with silica gel

Sources & evidence

ORD record
ord-14b11d884daf4a21a6f9d9435a014bf0
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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