Acetic Anhydride → HCID 86744579, compound

HRID 981315Notes

Reaction equation

HRID 981315 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[C:3]=1[C:4]([NH:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH:13]([CH3:33])[CH2:14][C:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:9][C@H:8]1[OH:34])=[O:5].[C:41](OC(=O)C)(=[O:43])[CH3:42]>C(O)(=O)C>[C:41]([NH:1][C:2]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[C:3]=1[C:4]([NH:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH:13]([CH3:33])[CH2:14][C:15]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:9][C@H:8]1[OH:34])=[O:5])(=[O:43])[CH3:42]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86744580HCID 86744580, compound

Product 1

HCID 86744579HCID 86744579, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2.72 parts of trans-4-[(2-amino-6-methoxybenzoyl)amino]-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide in 20 parts of acetic acid were added 0.56 parts of acetic acid anhydride. After stirring overnight at room temperature, the reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried at 80° C., yielding 2.45 parts (83.5%) of trans-4-[[2-(acetylamino)-6-methoxybenzoyl]amino]-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 146.5° C. (compound 61).

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 2,2'-oxybispropane
  7. filtrationThe product was filtered off
  8. customdried at 80° C.

Sources & evidence

ORD record
ord-6c1ceef2ad4e4988a03b84a4e5cace18
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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