Acetic Anhydride → HCID 14458456, compound

HRID 620219Notes

Reaction equation

HRID 620219 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1([CH2:18][O:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:21])[CH2:17][CH2:16][CH2:15][O:14]1)=[O:10].C(N(CC)CC)C.[C:48](OC(=O)C)(=[O:50])[CH3:49]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:48]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9]([O:11][CH2:12][C:13]1([CH2:18][O:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:21])[CH2:17][CH2:16][CH2:15][O:14]1)=[O:10])(=[O:50])[CH3:49]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14458455HCID 14458455, compound

Product 1

HCID 14458456HCID 14458456, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To 3.2 g (5.7 mmol) of the compound prepared in (b) above dissolved in 25 ml of chloroform was added, with stirring and under a nitrogen atmosphere, 18.15 g (180 mmol) of triethylamine, 11.63 g (114 mmol) of acetic anhydride and 0.035 g (0.29 mmol) of 4-dimethylaminopyridine. The resultant mixture was then heated to reflux and maintained at the reflux temperature for 72 hours. The volatiles were then removed under high vacuum and the resultant residue was dissolved in methylene chloride and washed rapidly with a saturated aqueous sodium bicarbonate solution. The organic layer was then dried over sodium sulfate, filtered and concentrated. The resultant residue was then chromatographed on silica gel employing a mixture of petroleum ether and ethyl acetate in a ratio of 1:1 by volume initially, with the product being eluted when the eluent was pure ethyl acetate. The resultant solution was then concentrated to obtain a semi-solid.

Workup

  1. additionwas added
  2. temperatureto reflux
  3. temperaturemaintained at the reflux temperature for 72 hours
  4. customThe volatiles were then removed under high vacuum
  5. dissolutionthe resultant residue was dissolved in methylene chloride
  6. washwashed rapidly with a saturated aqueous sodium bicarbonate solution
  7. dry with materialThe organic layer was then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resultant residue was then chromatographed on silica gel employing
  11. additiona mixture of petroleum ether and ethyl acetate in a ratio of 1:1 by volume initially
  12. washwith the product being eluted when the eluent
  13. concentrationThe resultant solution was then concentrated
  14. customto obtain a semi-solid

Sources & evidence

ORD record
ord-84115d7dc47d4cbf9d5491702ead554e
Source dataset
uspto-grants-1989_04
Patent number
US04820718

Reaction notes

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