Acetic Acid → HCID 131716974, compound

HRID 2248638Notes

Reaction equation

HRID 2248638 reaction equation
[NH2:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18](=[O:24])[N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:11][C@H:10]2[O:25][CH3:26])=[O:7])=[C:4]([O:30][CH3:31])[CH:3]=1.[C:32](O)(=[O:34])[CH3:33].[C:36](OC(=O)C)(=[O:38])[CH3:37].[OH-].[NH4+]>O>[OH2:7].[C:32]([NH:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18](=[O:24])[N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH2:11][C@H:10]2[O:25][CH3:26])=[O:7])=[C:4]([O:30][CH3:31])[CH:3]=1)(=[O:34])[CH3:33].[C:36]([NH:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[O:24])[CH2:11][C@H:10]2[O:25][CH3:26])=[O:7])=[C:4]([O:30][CH3:31])[CH:3]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 67922911HCID 67922911, compound

Product 1

HCID 131716974HCID 131716974, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4 parts of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[4-oxo-4-(1-pyrrolidinyl)butyl]-4-piperidinyl]benzamide in 20 parts of acetic acid were added 0,89 parts of acetic acid anhydride. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was poured into water and the whole was treated with ammonium hydroxide while cooling. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was solidified in a mixture of 2,2'-oxybispropane and a few drops of acetonitrile. The solid product was filtered off and crystallized from acetonitrile. After cooling to 0° C., the product was filtered off and dried in vacuo at 40° C., yielding 1.9 parts (42.8%) of cis-4-(acetylamino)-5-chloro-2-methoxy-N-[3-methoxy-1-[4-oxo-4-(1-pyrrolidinyl)butyl]-4-piperidinyl]benzamide hemihydrate; mp. 149.7° C. (compound 114).

Workup

  1. additionUpon complete addition
  2. temperaturewhile cooling
  3. extractionThe product was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. additionThe residue was solidified in a mixture of 2,2'-oxybispropane and a few drops of acetonitrile
  9. filtrationThe solid product was filtered off
  10. customcrystallized from acetonitrile
  11. filtrationthe product was filtered off
  12. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-2c34e2129f3b45f7b5fb6ddb5f93e300
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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