Acetic-formic anhydride → HCID 53850131, compound

HRID 2072469Notes

Reaction equation

HRID 2072469 reaction equation
[C:1](OC=O)(=[O:3])C.[OH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][C@H:9]1[CH2:21][N:22]1[CH2:38][CH2:37][C:25]2([N:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][NH:27][C:26]2=[O:36])[CH2:24][CH2:23]1>>[CH:1]([O:7][C@@H:8]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][C@H:9]1[CH2:21][N:22]1[CH2:23][CH2:24][C:25]2([N:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][NH:27][C:26]2=[O:36])[CH2:37][CH2:38]1)=[O:3]

Participants

3

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 53827185HCID 53827185, compound

Product 1

HCID 53850131HCID 53850131, compound

Procedure

To 0.11 mole of a stirred formic acid-acetic anhydride mixture (prepared as described in Rec. Trav. Chem., 83, 1287 (1964) is added 0.10 mole of trans-8-[(2,3-dihydro-1-hydroxy-5,6-dimethoxy-1H-inden-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one. The temperature of the reaction mixture is maintained below 20° C and stirring is continued for 12 days under argon. The reaction mixture is then poured, with stirring, into excess ice-cold aqueous sodium bicarbonate, extracted with ether and the ether extracts dried with anhydrous sodium sulfate. The ether is evaporated and the residue is crystallized from cyclohexane to give the title compound.

Workup

  1. temperatureThe temperature of the reaction mixture is maintained below 20° C
  2. additionThe reaction mixture is then poured
  3. stirringwith stirring, into excess ice-cold aqueous sodium bicarbonate
  4. extractionextracted with ether
  5. dry with materialthe ether extracts dried with anhydrous sodium sulfate
  6. customThe ether is evaporated
  7. customthe residue is crystallized from cyclohexane

Sources & evidence

ORD record
ord-b356a0f85b8646049eb7dc0b2d4eca1d
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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