Acetonitrile → (1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelate

HRID 375477

Reaction equation

HRID 375477 reaction equation
[C:1]([OH:11])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(#N)C.[C:15]1([C:21]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:29]3[CH:25]([CH2:26][NH:27][CH2:28]3)[S:24](=[O:30])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:1]([OH:11])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:31]1([C:21]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C@H:29]3[C@H:25]([CH2:26][NH:27][CH2:28]3)[S@:24](=[O:30])[CH2:23][CH2:22]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 439616(S)-mandelic acidHCID 18995289(-)-4,4-Diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide

Product 1

HCID 131719251(1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelateYield 14.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.5 g of (S)-mandelic acid and 90 cm3 of a mixture of acetonitrile and water (99/1 by volume) are added to 7.15 g of (1RS,4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide. After stirring, the resulting solution is allowed to stand for 48 hours at room temperature. The crystals obtained are drained, washed with the acetonitrile-water mixture and then dried. The crystals are taken up in 200 cm3 of a boiling acetonitrile-water mixture and after filtering while still hot, the solution obtained is allowed to stand for 5 hours at room temperature. The crystals are drained, washed twice with 10 cm3 of acetonitrile and then dried. 1.5 g of (1R*,4aR*,7aR*)4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelate are obtained; [α]D 20 =-228°, (c =0 44; acetic acid). The filtrate is allowed to stand for 20 hours at room temperature, the crystals obtained are drained, washed twice with 5 cm3 of acetonitrile and then dried. 0.62 g of (1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelate is obtained; [α]D 20 =-230°, (c =0.45; acetic acid).

Workup

  1. customThe crystals obtained
  2. washwashed with the acetonitrile-water mixture
  3. customdried
  4. filtrationafter filtering while still hot, the solution
  5. customobtained
  6. waitto stand for 5 hours at room temperature
  7. washwashed twice with 10 cm3 of acetonitrile
  8. customdried

Sources & evidence

ORD record
ord-fae7ff5d92294696a550c0c131ebaea4
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Linked notes

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