Acetic Anhydride → HCID 54319486, compound

HRID 1198765Notes

Reaction equation

HRID 1198765 reaction equation
[C:1]1([S:7][C:8]([CH:22]2[CH2:27][O:26][C:24](=[O:25])[CH:23]2[C:28](=[O:43])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:30]=2)([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:44][C:45](OC(C)=O)=[O:46].CCN(CC)CC.[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[C:45]([O:43][C:28](=[C:23]1[CH:22]([C:8]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:27][O:26][C:24]1=[O:25])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:30]=1)(=[O:46])[CH3:44]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 19103186HCID 19103186, compound

Product 1

HCID 54319486HCID 54319486, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the ketone from Step 1 (1.91 g) in CH2Cl2 (20 mL) was added Ac2O (1.5 mL), Et3N (2.3 mL) and DMAP (40 mg). The reaction mixture was stirred at r.t. for 18 hr then diluted with Et2O and a saturated solution of NH4Cl. The organic phase was extracted, washed with H2O, brine, dried over MgSO4, and the solvent evaporated to afford the title product as a foam which was used as such in the next step.

Workup

  1. extractionThe organic phase was extracted
  2. washwashed with H2O, brine
  3. dry with materialdried over MgSO4
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-05acddee407641a588771b5849a133e0
Source dataset
uspto-grants-1994_01
Patent number
US05281720

Reaction notes

Loading…