Dicyclohexylcarbodiimide → Cannabidiol (t-butyldimethylsilyloxy)acetate

HRID 2067148Notes

Reaction equation

HRID 2067148 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]([C@H:13]2[C@H:18]([C:19]([CH3:21])=[CH2:20])[CH2:17][CH2:16][C:15]([CH3:22])=[CH:14]2)=[C:10]([OH:12])[CH:11]=1.[Si:24]([O:31][CH2:32][C:33]([OH:35])=[O:34])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[C:9]([C@H:13]2[C@H:18]([C:19]([CH3:21])=[CH2:20])[CH2:17][CH2:16][C:15]([CH3:22])=[CH:14]2)=[C:8]([OH:23])[CH:7]=1.[Si:24]([O:31][CH2:32][C:33]([O-:35])=[O:34])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 644019CannabidiolHCID 11608070(t-Butyldimethylsilyloxy)acetic acid

Product 1

HCID 86627026Cannabidiol (t-butyldimethylsilyloxy)acetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of cannabidiol (125.8 mg, 0.4 mmol) and (t-butyldimethylsilyloxy)acetic acid (112.9 mg, 0.51 mmol) in dry dichloromethane (1 mL) was added of 4-dimethylaminopyridine (6.2 mg, 0.03 mmol) followed by N,N′-dicyclohexylcarbodiimide (123.8 mg, 0.6 mmol). The mixture was stirred at ambient temperature for 1 h. Additional amounts of the acid (26.6 mg) and N,N′-dicyclohexylcarbodiimide (31 mg) were added and stirring was continued for 1 h. Mixture was diluted with hexane (2 mL), filtered, and concentrated. The crude product was purified by preparative reverse phase HPLC (C8 column) with acetonitrile-water to afford cannabidiol (t-butyldimethylsilyloxy)acetate as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative reverse phase HPLC (C8 column) with acetonitrile-water

Sources & evidence

ORD record
ord-f67f05238c364e1e8112cdd895aec788
Source dataset
uspto-grants-2012_10
Patent number
US08293786B2

Reaction notes

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