Ethyl Acetate → HCID 178488040, compound

HRID 1593239Notes

Reaction equation

HRID 1593239 reaction equation
[CH3:1][O:2][C:3]1[CH:54]=[CH:53][C:6]2[N:7]=[C:8]([S:10]([C:13]3[CH:35]=[CH:34][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[O:20])=[C:15]([O:36][CH2:37][C:38]([O:40][CH2:41][CH2:42][S:43]([C:46]4[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=4)(=[O:45])=[O:44])=[O:39])[CH:14]=3)(=[O:12])=[O:11])[NH:9][C:5]=2[C:4]=1[S:55][CH2:56][C:57]1[C:62]([CH3:63])=[C:61]([O:64][CH3:65])[C:60]([CH3:66])=[CH:59][N:58]=1.ClC1C=C(C=CC=1)C(OO)=[O:72].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:54]=[CH:53][C:6]2[N:7]=[C:8]([S:10]([C:13]3[CH:35]=[CH:34][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][S:24]([C:27]4[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=4)(=[O:25])=[O:26])=[O:20])=[C:15]([O:36][CH2:37][C:38]([O:40][CH2:41][CH2:42][S:43]([C:46]4[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=4)(=[O:44])=[O:45])=[O:39])[CH:14]=3)(=[O:12])=[O:11])[NH:9][C:5]=2[C:4]=1[S:55]([CH2:56][C:57]1[C:62]([CH3:63])=[C:61]([O:64][CH3:65])[C:60]([CH3:66])=[CH:59][N:58]=1)=[O:72]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 178488039HCID 178488039, compound

Product 1

HCID 178488040HCID 178488040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(4-Tolylsulfonyl)ethyl 4-[{5-methoxy-([4-methoxy-3,5-dimethyl(2-pyridyl)]methylthio)benzimidazolyl}sulfonyl]-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate (Intermediate A20, 4.8 g, 0.0054 mol) was dissolved in 20 mL of tetrahydrofuran, and the solution was left in a freezer for 40 min. A solution of 3-chloroperoxybenzoic acid (1.3 g, 0.0075 mol) in 6 mL of tetrahydrofuran was cooled for 30 min. The two were combined and left in the freezer for 16 hr. The mixture was then poured into a rapidly stirring mixture of 5% aqueous sodium metabisulfite and ethyl acetate. The layers were separated, and the organic layer was washed with 2 portions of 2.5% aqueous sodium bicarbonate and with saturated aqueous sodium chloride. The solution was filtered through 1PS paper and concentrated at aspirator pressure. The residue was separated on a column of flash silica gel (2:1 ethyl acetate:hexanes→ethyl acetate)to yield 2.0 g (41%) of the title compound.

Workup

  1. waitleft in the freezer for 16 hr
  2. additionThe mixture was then poured into
  3. customThe layers were separated
  4. washthe organic layer was washed with 2 portions of 2.5% aqueous sodium bicarbonate and with saturated aqueous sodium chloride
  5. filtrationThe solution was filtered through 1PS paper
  6. concentrationconcentrated at aspirator pressure
  7. customThe residue was separated on a column of flash silica gel (2:1 ethyl acetate:hexanes→ethyl acetate)to yield 2.0 g (41%) of the title compound

Sources & evidence

ORD record
ord-dec8f0eac4ab4d12a92e6a2a25e38d68
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

Loading…