Citric Acid → HCID 10182601, compound

HRID 2396156Notes

Reaction equation

HRID 2396156 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([CH2:8][C:9](O)=O)(C(O)=O)O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]([C:26](=[O:41])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=1)[C:21](=O)[CH2:20][CH2:19]2.[CH2:43](C(C)=O)C>CC(C)=O>[C:1]1([C:21]2[CH2:20][CH2:19][C:18]3[C:23]([C:22]=2[C:26](=[O:41])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:29][CH:28]=2)=[CH:24][CH:25]=[C:16]([O:15][CH3:14])[CH:17]=3)[CH:2]=[CH:3][CH:8]=[CH:9][CH:43]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6569Methyl Ethyl KetoneHCID 12835038HCID 12835038, compound

Product 1

HCID 10182601HCID 10182601, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

The aqueous mixture was rendered alkaline by addition of base, and the alkaline mixture was extracted with ethyl acetate. The extract was dried and concentrated to obtain 8.7 grams of product which was dissolved in acetone, and one equivalent of citric acid was added to the mixture. The acetone was stripped off, and methyl ethyl ketone was added to the residue. The mixture was maintained at 0° C. overnight, and the crystals which formed were collected by filtration and washed with cold methyl ethyl ketone and vacuum dried. The solid was recrystallized from acetone to obtain the title compound in the form of its citrate salt. mp 98°-100° C.

Workup

  1. customthe crystals which formed
  2. filtrationwere collected by filtration
  3. washwashed with cold methyl ethyl ketone and vacuum
  4. customdried
  5. customThe solid was recrystallized from acetone

Sources & evidence

ORD record
ord-e044e916ac494148b1aec9b9a978bfc1
Source dataset
uspto-grants-1996_02
Patent number
US05491140

Reaction notes

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