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

HRID 375479

Reaction equation

HRID 375479 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.O.[C:16]1([C:22]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[S:25](=[O:31])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C.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:32]1([C:22]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:30]3[C@H:26]([CH2:27][NH:28][CH2:29]3)[S@:25](=[O:31])[CH2:24][CH2:23]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 962Water2×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 19.6%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

15.8 g of (S)-(+)-mandelic acid and 750 cm3 of a mixture of acetonitrile and water (99/1 by volume) are added to 32.3 g of (1RS,4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide, followed by 5.0 cm3 of water. After making lukewarm, the solution obtained is allowed to stand for 48 hours at room temperature. The crystalline suspension is filtered, and the filtrate, concentrated to dryness, gives a meringue which is taken up in 200 cm3 of the boiling acetonitrile-water mixture. The solution obtained is allowed to stand for about 20 hours at room temperature. The crystals are drained, washed with acetonitrile, dried and then again taken up in 200 cm3 of an acetonitrile-water mixture (98/2 by volume). The resulting solution is allowed to stand for about 20 hours at room temperature. The crystals are drained and dried. 9.4 g of (1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-(+)-mandelate are obtained; [α]D 20 =+337°(c=0 45; acetic acid)

Workup

  1. customthe solution obtained
  2. filtrationThe crystalline suspension is filtered
  3. concentrationthe filtrate, concentrated to dryness
  4. customgives a meringue which
  5. customThe solution obtained
  6. waitto stand for about 20 hours at room temperature
  7. washwashed with acetonitrile
  8. customdried
  9. waitto stand for about 20 hours at room temperature
  10. customdried

Sources & evidence

ORD record
ord-582138e39e59410d84c0c27bb8898715
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Linked notes

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