Sulfuric Acid → HCID 178526200, compound

HRID 1447457Notes

Reaction equation

HRID 1447457 reaction equation
C([N:9]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@H:10]1[C:11]([OH:13])=[S:12])(=O)C1C=CC=CC=1.S(=O)(=O)(O)O.C(OCC(C)C)(=O)C.[OH-].[Na+]>O.C(O)(=O)C>[C:17]1([C@@H:15]2[CH2:16][NH:9][C@H:10]([C:11]([OH:13])=[S:12])[CH2:14]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8038Isobutyl AcetateHCID 14798Sodium HydroxideHCID 178519530HCID 178519530, compound

Product 1

HCID 178526200HCID 178526200, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The N-benzoyl-cis-4-phenylthio-L-proline is heated on a steam bath and 0.5 liters of glacial acetic acid are added. The mixture is swirled and 0.5 liters of water followed by 100 ml. of concentrated sulfuric acid are added. The turbid mixture is heated at reflux at an oil bath temperature of about 125° and maintained at reflux until the reaction is completed. The reaction liquid is cooled to room temperature and 0.75 liters of isobutyl acetate and 3 kg. of cracked ice are added with brisk agitation. 50 g. of concentrated aqueous sodium hydroxide solution are added and the product is collected and washed with methanol. The product is further purified by dissolution in aqueous sodium hydroxide, treatment with activated carbon, filtration, and careful crystallization with HCl. The crystals are collected, washed with water, and dried to yield cis-4-phenyl-thio-L-proline as a white crystalline powder; m.p. 240° (d); [α]D23 -118° (C=1, N sodium hydroxide).

Workup

  1. temperatureThe turbid mixture is heated
  2. temperatureat reflux at an oil bath temperature of about 125°
  3. temperaturemaintained
  4. temperatureat reflux until the reaction
  5. customThe reaction liquid
  6. additionof cracked ice are added with brisk agitation
  7. customthe product is collected
  8. washwashed with methanol
  9. customThe product is further purified by dissolution in aqueous sodium hydroxide
  10. filtrationtreatment with activated carbon, filtration, and careful crystallization with HCl
  11. customThe crystals are collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-4f22f98d49f74edd8d951fb9bb31885b
Source dataset
uspto-grants-1982_02
Patent number
US04316906

Reaction notes

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