Acetic Anhydride → HCID 54319486, compound

HRID 483827Notes

Reaction equation

HRID 483827 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-bf42baa5f57d4f279ceda100c4dda305
Source dataset
uspto-grants-1993_07
Patent number
US05227399

Reaction notes

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