Acetic Anhydride → HCID 20562575, compound

HRID 1155099Notes

Reaction equation

HRID 1155099 reaction equation
[CH:1]1([C:4]([N:6]2[CH:13]3[CH2:14][N:9]([C:10]4[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:11]=4[CH2:12]3)[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[CH:1]1([C:4]([N:6]2[CH:13]3[CH2:14][N:9]([C:10]4[CH:18]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:15][C:11]=4[CH2:12]3)[CH2:8][CH2:7]2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12764424HCID 12764424, compound

Product 1

HCID 20562575HCID 20562575, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-cyclopropanecarbonyl-9-amino-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (8 g.) and acetic anhydride (50 ml.) was heated on a steam bath for two hours. Pyridine was added and heating was continued for three hours. The mixture was concentrated to dryness. The residue was partitioned between aqueous base and chloroform. The chloroform layer was dried and concentrated to dryness. Recrystallization of the residue from acetonitrile afforded a product (m.r. 117°-187° C.), which to remove product of diacetylation was warmed with dilute aqueous sodium bicarbonate. Extraction of the resulting mixture with chloroform and concentration of the chloroform extract to dryness afforded 4-cyclopropanecarbonyl-9-acetamido-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (about 8 g.), the compound of Formula VI wherein Q' is cyclopropanecarbonyl and R"CONH is acetamido.

Workup

  1. temperaturewas heated on a steam bath for two hours
  2. temperatureheating
  3. concentrationThe mixture was concentrated to dryness
  4. customThe residue was partitioned between aqueous base and chloroform
  5. dry with materialThe chloroform layer was dried
  6. concentrationconcentrated to dryness
  7. customRecrystallization of the residue from acetonitrile
  8. customafforded a product (m.r. 117°-187° C.), which
  9. customto remove product of diacetylation
  10. temperaturewas warmed with dilute aqueous sodium bicarbonate
  11. extractionExtraction of the resulting mixture with chloroform and concentration of the chloroform
  12. extractionextract to dryness

Sources & evidence

ORD record
ord-aa8e1faf540a4f7bacee27c629f0920a
Source dataset
uspto-grants-1981_11
Patent number
US04299830

Reaction notes

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