Valeryl chloride → HCID 53814910, compound

HRID 1768661Notes

Reaction equation

HRID 1768661 reaction equation
[C:1]([CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[C:16]([CH2:19][NH:20][C@H:21]([C:25]([OH:27])=[O:26])[CH:22]([CH3:24])[CH3:23])[CH:17]=[CH:18][C:5]1=2)#[N:2].[C:28](Cl)(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32]>ClCCl.C(N(C(C)C)CC)(C)C>[C:1]([CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[C:16]([CH2:19][N:20]([C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32])[C@H:21]([C:25]([OH:27])=[O:26])[CH:22]([CH3:23])[CH3:24])[CH:17]=[CH:18][C:5]1=2)#[N:2]

Participants

5

Reactant 2

HCID 61186Valeryl chlorideHCID 54419178HCID 54419178, compound

Product 1

HCID 53814910HCID 53814910, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

Compound 40-b (1.2 g) was dissolved in a mixture of 30 ml of dichloromethane and 0.6 ml of diisopropylethylamine, and 0.4 ml of valeryl chloride was added to the solution under ice cooling, followed by stirring at room temperature for 5 hours. Then, ice was added thereto, and the mixture was stirred for some time. The mixture was diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (5/1)] to give 1.4 g (96%) of the product as a yellow oily substance.

Workup

  1. additionwas added to the solution under ice cooling
  2. additionThen, ice was added
  3. stirringthe mixture was stirred for some time
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (5/1)]

Sources & evidence

ORD record
ord-c121077f590b4108921416bf636bb011
Source dataset
uspto-grants-1995_01
Patent number
US05378701

Reaction notes

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