1-Chloroethyl Cyclohexyl Carbonate → HCID 86628911, compound

HRID 1919442Notes

Reaction equation

HRID 1919442 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[C@@H:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](OC)=[CH:19][CH:18]=1)[C:12]([OH:14])=[O:13])(=[O:7])=[O:6].[CH:27]1([O:33][C:34]([O:36][CH:37](Cl)[CH3:38])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:25])([CH3:26])[C@@H:11]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:12]([O:14][CH2:38][CH2:37][O:36][C:34]([O:33][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:35])=[O:13])(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 86628873HCID 86628873, compound

Product 1

HCID 86628911HCID 86628911, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoic acid (11) (0.4 g, 1.0 mmol) dissolved in 5 mL of anhydrous toluene was reacted with 0.67 g (4.0 mmol) of 1-chloroethyl cyclohexyloxyformate in the presence of 0.55 g (2.0 mmol) of silver carbonate (Ag2CO3). After work-up, the crude product was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:4) as eluent to provide 0.41 g (71% yield) of the title compound (43a). Rf=0.40 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.06-1.08 (m, 6H), 1.25-1.58 (br. m, 9H), 1.73-1.78 (br. m, 2H), 1.88-1.95 (br. m, 2H), 2.24-2.31 (m, 2H), 3.20-3.25 (m, 2H), 3.63-3.66 (m, 2H), 3.84-3.85 (2s, 1H), 3.94-3.97 (2d, J=9.2, 8.8 Hz, 1H), 4.19-4.23 (2d, J=9.2, 8.8 Hz, 1H), 4.33-4.38 (2d, J=11.2, 11.6 Hz, 1H), 4.55-4.70 (m, 2H), 6.81-6.87 (m, 1H), 7.31-7.37 (m, 5H) ppm. MS (ESI) m/z 571.05 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up, the crude product was purified by silica gel column chromatography
  2. additiona mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:4) as eluent

Sources & evidence

ORD record
ord-a67e12e7c3634bddb268324e764aa621
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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