Acetic Acid → HCID 86688089, compound

HRID 407910Notes

Reaction equation

HRID 407910 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:13]1[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14]1)[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([SH:23])[CH3:22].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOCC>[CH2:1]([O:8][C@H:9]([C@@H:13]1[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14]1)[C:10](=[O:12])[S:23][CH2:21][CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6343EthanethiolHCID 10868DicyclohexylcarbodiimideHCID 67470545HCID 67470545, compound

Product 1

HCID 86688089HCID 86688089, compoundYield 15.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Crude (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid (13 g, 46 mmol) was dissolved in CH2Cl2 (150 mL) and cooled in an ice bath. Ethanethiol (6.9 mL, 93 mmol) and N,N-dimethylpyridin-4-amine (0.11 g, 0.93 mmol) were added followed by DCC (11 g, 56 mmol). This mixture was stirred in ice bath and allowed to slowly warm to ambient temperature overnight. Acetic acid (15 mL) was added and the reaction was stirred for 10 minutes. The reaction mixture was poured into vigorously stirring ether (400 mL) and then filtered. The filtrate was washed with 10% sodium carbonate, water, 0.5 N HCl, water, brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified over silica gel (1-5% EtOAc in hexanes) to afford (R)—S-ethyl 2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (2.3 g, 7.1 mmol, 15% yield) as a yellow oil.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction was stirred for 10 minutes
  3. filtrationfiltered
  4. washThe filtrate was washed with 10% sodium carbonate, water, 0.5 N HCl, water, brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified over silica gel (1-5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c5d9c538026d414e995d86b476942dae
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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