Benzyl Alcohol → HCID 178462210, compound

HRID 2205191Notes

Reaction equation

HRID 2205191 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@H:6]([C:8]([OH:10])=[O:9])[CH3:7].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl-:3].[CH2:11]([O:9][C:8](=[O:10])[C@@H:6]([NH3+:5])[CH3:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 5950L-AlanineHCID 24386Thionyl Chloride

Product 1

HCID 178462210HCID 178462210, compound

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (27 mL) was added drop-wise to a solution L-alanine (42) (6.83 g, 76.6 mmol) in benzyl alcohol (120 mL). After stirring at 0° C. for 2 h, the reaction mixture was warmed to room temperature and stirred for a further 24 h and then evaporated to dryness under reduced pressure. Trituration with diethyl ether, followed by filtration and evaporation under reduced pressure, provided the crude product 43 (3.5 g), which was used directly without further purification. LC-MS (M-Cl)+=180

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred for a further 24 h
  3. customevaporated to dryness under reduced pressure
  4. filtrationTrituration with diethyl ether, followed by filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-2535ce0fffd54aea840acbbc2e12a416
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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