58304-47-5 → HCID 86628914, compound

HRID 1919445Notes

Reaction equation

HRID 1919445 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([C:33]([O:35][CH:36](Cl)[CH3:37])=[O:34])[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][CH2:37][CH2:36][O:35][C:33]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:34])=[O:13])(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 1359282058304-47-5HCID 86628873HCID 86628873, compound

Product 1

HCID 86628914HCID 86628914, compoundYield 39.2%

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) (1.2 g, 3.3 mmol) dissolved in 10 mL of anhydrous toluene was reacted with 1.9 g (10.0 mmol) of chloroethyl cyclohexanecarboxylate (24) in the presence of 1.4 g (5.0 mmol) of silver carbonate (Ag2CO3). After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:9→EtOAc/Hxn=1:5) as eluent to provide 0.69 g (39% yield) of the title compound (44a) as a colorless oil. Rf=0.11 (EtOAc/Hxn=1:9). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.06-1.08 (m, 6H), 1.23-1.36 (br. m, 3H), 1.44-1.50 (br. m, 2H), 1.53 (d, J=5.6 Hz, 3H), 1.58-1.68 (br. m, 1H), 1.74-1.80 (br. m, 2H), 1.86-1.97 (br. m, 2H), 2.25-2.39 (m, 3H), 3.21-3.26 (m, 2H), 3.63-3.66 (m, 2H), 3.82-3.84 (2s, 1H), 3.96 (d, J=9.2 Hz, 1H), 4.20-4.24 (m, 1H), 4.33-4.37 (2d, J=11.6, 11.6 Hz, 1H), 4.59-4.66 (2d, J=10.8, 11.2 Hz, 1H), 6.91-6.95 (m, 1H), 7.30-7.37 (m, 5H) ppm. MS (ESI) m/z 554.92 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up, the crude material was purified by silica gel column chromatography
  2. additiona mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:9→EtOAc/Hxn=1:5) as eluent

Sources & evidence

ORD record
ord-9470f49e61784048b9b83b9ebba946f8
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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