Thionyl Chloride → HCID 12924680, compound

HRID 1193472Notes

Reaction equation

HRID 1193472 reaction equation
[S:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].S(Cl)([Cl:19])=O>CCCCCC>[S:1]([NH:11][C@H:12]([C:14]([Cl:19])=[O:16])[CH3:13])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 737622N-Tosyl-L-alanine

Product 1

HCID 12924680HCID 12924680, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-tosyl-L-alanine (3.1 g; 13 mmol) and thionyl chloride (6 mL) was heated for 1.5 hours at 50° C. then diluted with dry hexane (50 mmL). The mixture was stirred rapidly, chilled and the solid was collected by filtration to obtain 3.15 g (93%) of N-tosyl-L-alaninyl chloride (35) having a melting point of 99°-100° C. The IR spectrum of this material was identical to that of the recrystallized material prepared according to method (i).

Workup

  1. temperaturechilled
  2. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-24ea0215d2664fcda5ccf5c1f8f5346c
Source dataset
uspto-grants-1989_03
Patent number
US04810636

Reaction notes

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