Acetic Anhydride → HCID 54233282, compound

HRID 1576069Notes

Reaction equation

HRID 1576069 reaction equation
[NH2:1][C:2]1[CH:3]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[S:4][CH2:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].Cl(O)(=O)(=O)=O.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([NH:1][C:2]1[CH:3]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[S:4][CH2:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24247Perchloric AcidHCID 131710448HCID 131710448, compound

Product 1

HCID 54233282HCID 54233282, compoundYield 100%

Procedure

To a solution of 7.4 g (.0226 mole) of 3-amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid piperidide in 50 ml of acetic anhydride was added dropwise 1 ml of perchloric acid. The reaction was stirred for 1.5 hrs. and then was worked up. Acetic anhydride was removed under vacuum. The residue was partitioned between 50 ml of 10% by weight aqueous sodium bicarbonate solution and 150 ml of methylene chloride. The basic, aqueous phase was extracted three times with 30 ml portions of methylene chloride. The methylene chloride phase was dried over sodium sulfate, filtered, and evaporated to yield 8.2 g (0.022 mole, 100%) of 3-acetamido-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid piperidide.

Workup

  1. customAcetic anhydride was removed under vacuum
  2. customThe residue was partitioned between 50 ml of 10% by weight aqueous sodium bicarbonate solution and 150 ml of methylene chloride
  3. extractionThe basic, aqueous phase was extracted three times with 30 ml portions of methylene chloride
  4. dry with materialThe methylene chloride phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a3c0b505281d4cd990e50bbc6f7262d4
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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