Diisopropylethylamine → 1-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1429154Notes

Reaction equation

HRID 1429154 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:12][C:13]([C:15]1([NH:20][C:21]([CH:23]2[CH2:27][CH:26]([OH:28])[CH2:25][CH:24]2[C:29]([OH:31])=O)=[O:22])[CH2:17][CH:16]1[CH:18]=[CH2:19])=[O:14])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][NH:57][CH2:58][CH2:59][CH2:60][CH2:61][CH:62]=[CH2:63].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:10]([O:12][C:13]([C:15]1([NH:20][C:21]([CH:23]2[CH2:27][CH:26]([OH:28])[CH2:25][CH:24]2[C:29](=[O:31])[N:57]([CH2:58][CH2:59][CH2:60][CH2:61][CH:62]=[CH2:63])[CH3:56])=[O:22])[CH2:17][CH:16]1[CH:18]=[CH2:19])=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17825054N-Methylhex-5-en-1-amineHCID 668702712-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-cyclopentane carboxylic acid diisopropylethylamine salt

Product 1

HCID 668706071-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The crude compound 10b (5.5 mol) was dissolved in DCM (50 mL) and DMF (14 mL) followed by addition of HATU (2.09 g, 5.5 mmol), N-methyl-N-hex-5-enylamin (678 mg, 6.0 mmol) and DIPEA (3.08 mL, 17.5 mmol) at room temperature. The reaction was stirred at ambient temperature for 1 h. LC/MS analysis showed complete conversion of the starting materials and the reaction mixture was concentrated in vacuo. The residue was redissolved in EtOAc (100 mL) and the organic phase washed with 0.1 M HCl (aq), K2CO3 (aq) and brine, dried (MgSO4) and filtered. Removal of the solvent in vacuo gave an oil which was purified by flash chromatography (Silica, EtOAc:MeOH) to afford the title compound (1.65 g, 74%). TLC (Silica): MeOH:EtOAc 5:95, Rf=0.5; LC/MS >95%, m/z (ESI+)=407 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was redissolved in EtOAc (100 mL)
  3. washthe organic phase washed with 0.1 M HCl (aq), K2CO3 (aq) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customRemoval of the solvent in vacuo
  7. customgave an oil which
  8. customwas purified by flash chromatography (Silica, EtOAc:MeOH)

Sources & evidence

ORD record
ord-000d71b3b9984ae583af53d2725cc36d
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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