Diisopropylethylamine → HCID 86706343, compound

HRID 1396865Notes

Reaction equation

HRID 1396865 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[NH:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH:28]([N:30]([CH2:39][C@@H:40]([CH2:44][CH2:45][CH2:46][CH3:47])[C:41](F)=[O:42])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29]>CN(C=O)C.C(OCC)(=O)C>[CH:28]([N:30]([CH2:39][C@@H:40]([CH2:44][CH2:45][CH2:46][CH3:47])[C:41]([N:12]1[C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10])=[O:42])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:29]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 537448401-(Benzyloxy carbonyl)pyrazolidine-3-carboxylic acidHCID 86706342HCID 86706342, compound

Product 1

HCID 86706343HCID 86706343, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid 91.52 g, 6.1 mmol) and DIPEA (3.15 g, 24.4 mmol) in DMF (8 mL) was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl fluoride (10) (1.7 g, 6.1 mmol) in DMF. The reaction mixture was stirred at rt overnight and LC/MS indicated completion of the reaction. The mixture was diluted with ethyl acetate (20 mL), and washed with 5% aqueous citric acid, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:1) followed by DCM/MeOH (200:1) to provide the title compound (0.48 g, 32%). LCMS: (M+H)+: 512.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.79 (t, J=6.0 Hz, 3H), 1.10 (m, 4H), 1.40 (m, 1H), 1.57 (m, 1H), 1.77 (m, 1H), 2.17 (m, 1H), 2.97 (m, 2H), 3.25-3.69 (m, 1H), 4.13 (m, 3H), 4.56-4.93 (m, 2H), 5.12 (s, 2H), 7.34 (m, 10H), 7.74 (s, 0.3H), 8.36 (s, 0.6H).

Workup

  1. customcompletion of the reaction
  2. washwashed with 5% aqueous citric acid, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-fbc0dcf0d59c4c268b362ee20ac6fe27
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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