2-Methoxyphenylacetic acid → (4aRS,7aRS)-4,4-diphenyl-6-[(2-methoxyphenyl)acetyl]perhydrothiopyrano[2,3-c]pyrrole

HRID 375492

Reaction equation

HRID 375492 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.Cl.[C:14]1([C:20]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:28]3[CH:24]([CH2:25][NH:26][CH2:27]3)[S:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[C:29]1([C:20]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:28]3[CH:24]([CH2:25][N:26]([C:10](=[O:12])[CH2:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:27]3)[S:23][CH2:22][CH2:21]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 67745331(4aRS,7aRS)4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride

Product 1

HCID 67745346(4aRS,7aRS)-4,4-diphenyl-6-[(2-methoxyphenyl)acetyl]perhydrothiopyrano[2,3-c]pyrroleYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.13 g of N,N'-carbonyldiimidazole are added to a solution, cooled to 0° C., of 1.16 g of 2-methoxyphenylacetic acid in 20 cm3 of dry dichloromethane. The mixture is stirred for 40 minutes at 0° C. and then a solution of 2.15 g of (4aRS,7aRS)4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride and 0.9 cm3 of triethylamine in 20 cm3 of dichloromethane is added. The reaction mixture is stirred for one hour at 0° C. and is then washed with a saturated aqueous solution of sodium hydrogen carbonate. The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is washed with 30 cm3 of ethyl ether and 30 cm3 of diisopropyl oxide and it is then dried under reduced pressure (2.7 kPa). 2.66 g of (4aRS,7aRS)-4,4-diphenyl-6-[(2-methoxyphenyl)acetyl]perhydrothiopyrano[2,3 -c]pyrrole are obtained in the form of a white solid; melting point 172° C.

Workup

  1. stirringThe reaction mixture is stirred for one hour at 0° C.
  2. washis then washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe solid obtained
  6. washis washed with 30 cm3 of ethyl ether and 30 cm3 of diisopropyl oxide and it
  7. customis then dried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-2680172248a14bcda158531c8b039243
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Linked notes

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