Diethyl Ether → HCID 53764774, compound

HRID 904489Notes

Reaction equation

HRID 904489 reaction equation
FC(F)(F)C([N:5]([CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.CCOCC.[C:43]([CH:48]([CH:50]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[OH:51])[OH:49])([O:45][CH2:46][CH3:47])=[O:44]>C(=O)([O-])[O-].[K+].[K+]>[CH2:15]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:51][CH:50]([CH:48]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[OH:49])[C:52]([O:54][CH2:55][CH3:56])=[O:53])=[O:11])=[CH:13][CH:14]=1)[CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 54406239HCID 54406239, compound

Product 1

HCID 53764774HCID 53764774, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

N-trifluoroacetyl-4-(4-tetradecenylamino)benzoyl chloride and 1.2 g. triethylamine in 100 ml. warm ether is treated with 2.5 g. diethyl tartrate and refluxed for 24 hours. The hot solution is filtered, the residue is washed with hot ether, and the solvent evaporated from the combined filtrate and washings to yield a solid residue. After dissolving in aqueous methanolic potassium carbonate, the product is precipitated by acidification, filtered, and dried. Crystallization from acetone yields the diethyl tartrate as a white, crystalline solid.

Workup

  1. filtrationThe hot solution is filtered
  2. washthe residue is washed with hot ether
  3. customthe solvent evaporated from the combined filtrate and washings
  4. customto yield a solid residue
  5. customthe product is precipitated by acidification
  6. filtrationfiltered
  7. customdried
  8. customCrystallization from acetone

Sources & evidence

ORD record
ord-e8d187cce8a34aac90e974e42cb97471
Source dataset
uspto-grants-1980_10
Patent number
US04230878

Reaction notes

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