Acetic Anhydride → HCID 57929330, compound

HRID 1024109Notes

Reaction equation

HRID 1024109 reaction equation
[CH3:1][C:2](OC(C)=O)=[O:3].CCN(CC)CC.[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH2:24][CH2:25][CH2:26][C@@H:27]2[C@@H:31]([C:32]3[CH:37]=[CH:36][C:35]([CH:38]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=4)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:34][CH:33]=3)[C:30](=[O:54])[CH:29]([OH:55])[CH:28]2[OH:56])=[CH:22][CH:23]=1)=[O:18].[C:57](OCC)(=[O:59])[CH3:58]>CN(C1C=CN=CC=1)C.C(Cl)CCl>[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH2:24][CH2:25][CH2:26][C@@H:27]2[C@@H:31]([C:32]3[CH:37]=[CH:36][C:35]([CH:38]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=4)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:34][CH:33]=3)[C:30](=[O:54])[CH:29]([O:55][C:2](=[O:3])[CH3:1])[CH:28]2[O:56][C:57](=[O:59])[CH3:58])=[CH:22][CH:23]=1)=[O:18]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 57929337HCID 57929337, compound

Product 1

HCID 57929330HCID 57929330, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Ac2O (100 μL, 1.06 mmol), Et3N (160 μL, 1.15 mmol) and DMAP (26 mg, 0.21 mmol) were added to a solution of the diol (27, 55 mg, 0.093 mmol) in ClCH2CH2Cl (0.5 mL). The reaction was stirred overnight, diluted with ethyl acetate and then washed with 1 M HCl, saturated NaHCO3, and brine. The ethyl acetate solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/hexanes) provided the title compound (32 mg, 51%).

Workup

  1. washwashed with 1 M HCl, saturated NaHCO3, and brine
  2. dry with materialThe ethyl acetate solution was then dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-545a5381adf249608aa4a7adac857be1
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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