Benzyl Alcohol → HCID 131713592, compound

HRID 1463021Notes

Reaction equation

HRID 1463021 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:11])=O.[C:13]1([S:19][C@@H:20]2[CH2:24][NH:23][C@H:22]([C:25](O)=[O:26])[CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[ClH:11].[C:13]1([S:19][C@@H:20]2[CH2:24][NH:23][C@H:22]([C:25]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:26])[CH2:21]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 11379084cis-4-phenylthio-l-prolin

Product 1

HCID 131713592HCID 131713592, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Six hundred ml. of benzyl alcohol are cooled to 10° and, with vigorous stirring, there is added over the course of 30 minutes, 100 grams of thionyl chloride, while the temperature is maintained at 10°. To this solution there is added, at 10°, 50 grams of cis-4-(phenylthio)-L-proline and the mixture stirred for 48 hours at room temperature. To this reaction mixture there is then added 4 liters of anhydrous ether and the mixture stirred vigorously with cooling. The precipitated solid is filtered, washed with ether and dried to yield the desired 4-(S)-(phenylthio)-L-proline, phenylmethyl ester hydrochloride salt.

Workup

  1. temperatureis maintained at 10°
  2. additionTo this solution there is added, at 10°
  3. temperaturewith cooling
  4. filtrationThe precipitated solid is filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-9281d18e67d945ab96d6a1ad90a307dc
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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