Acetyl chloride → HCID 67461057, compound

HRID 554486Notes

Reaction equation

HRID 554486 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:11][C:10]1([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[CH:42]=1)[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:63](Cl)(=[O:65])[CH3:64].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl.C(OC(=O)C)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:11][C:10]1([O:40][C:63](=[O:65])[CH3:64])[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][C:48]2[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=2)[CH:42]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67460415HCID 67460415, compound

Product 1

HCID 67461057HCID 67461057, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of [2R,3S,4R,5R]-2,3,4-trisbenzyloxy-5-benzyloxymethyl-1-[3-(4-methoxybenzyl)phenyl]cyclohexanol (20 mg), triethylamine (0.008 mL) and 4-dimethylamino-pyridine (0.7 mg) in dichloromethane (0.10 mL), acetic anhydride (0.003 mL) was added under cooling with ice and the reaction mixture was stirred at room temperature for two hours. Then, acetyl chloride (0.003 mL) was added thereto under cooling with ice and the reaction mixture was stirred at room temperature for 30 minutes. a saturated sodium hydrogen-carbonate aqueous solution was added thereto and the mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated and the obtained residue was purified by preparative TLC [developing solution=ethyl acetate:n-hexane (2:5)] to obtain the title compound (4.2 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. customthe obtained residue was purified by preparative TLC [developing solution=ethyl acetate:n-hexane (2:5)]

Sources & evidence

ORD record
ord-b32082ce81f74ae48370f33a4acffaf9
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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