Acetone → HCID 131719041, compound

HRID 1647764Notes

Reaction equation

HRID 1647764 reaction equation
[CH3:1][CH:2]([CH3:35])[CH2:3][O:4][C:5](=[O:34])[CH2:6][NH:7][C:8](=[O:33])[C@H:9]([CH2:17][N:18]1[CH2:23][CH2:22][C@:21]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)([CH3:24])[C@@H:20]([CH3:32])[CH2:19]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:36]([OH:44])(=[O:43])[C@H:37]([CH2:39][C:40]([OH:42])=[O:41])[OH:38].[CH3:45]C(C)=O>C(OCC)(=O)C>[C:36]([OH:44])(=[O:43])[CH:37]([CH2:39][C:40]([OH:42])=[O:41])[OH:38].[CH3:45][CH:3]([O:4][C:5](=[O:34])[CH2:6][NH:7][C:8](=[O:33])[C@H:9]([CH2:17][N:18]1[CH2:23][CH2:22][C@:21]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)([CH3:24])[C@@H:20]([CH3:32])[CH2:19]1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:2][CH3:1].[C:36]([OH:44])(=[O:43])[CH:37]([CH2:39][C:40]([OH:42])=[O:41])[OH:38].[C:36]([OH:44])(=[O:43])[CH:37]([CH2:39][C:40]([OH:42])=[O:41])[OH:38].[OH:31][C:27]1[CH:26]=[C:25]([C@:21]2([CH3:24])[CH2:22][CH2:23][N:18]([CH2:17][C@H:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([NH:7][CH2:6][C:5]([O:4][CH:3]([CH3:36])[CH2:2][CH3:35])=[O:34])=[O:33])[CH2:19][C@@H:20]2[CH3:32])[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 222656L-Malic Acid2×HCID 9871231HCID 9871231, compound

Product 1

HCID 131719041HCID 131719041, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A compound of Example 1, (2.5 g, 5.2 mmol, 1.0 equiv) was dissolved in 50 mL of ethyl acetate. L-malic acid (1.03 g, 7.8 mmol, 1.5 eq) was added to the mixture. After the L-malic acid was dissolved by stirring, the solution was heated to 70° C. and 4.0 mL of acetone was added. The solution was crystallized. The product was isolated by filtration. The filter cake was washed with ethyl acetate. The salt was dried until the ethyl acetate levels were below 1%. The title compound was isolated as a white crystal. The sample was analyzed using x-ray powder diffraction. mp 94°-950C.

Workup

  1. customThe solution was crystallized
  2. customThe product was isolated by filtration
  3. washThe filter cake was washed with ethyl acetate
  4. dry with materialThe salt was dried until the ethyl acetate levels

Sources & evidence

ORD record
ord-18b0787fd8154d95a574992f90ab913a
Source dataset
uspto-grants-1995_07
Patent number
US05434171

Reaction notes

Loading…