Benzyl Alcohol → D-Homophenylalanine Benzyl ester Tosylate

HRID 1365885Notes

Reaction equation

HRID 1365885 reaction equation
Cl.[NH2:2][C@@H:3]([C:12]([OH:14])=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>C1C=CC=CC=1>[S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)([OH:33])(=[O:32])=[O:31].[CH2:15]([O:13][C:12](=[O:14])[C@@H:3]([CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 66963526D-(R)-Homophenylalanine HCl

Product 1

HCID 86602419D-Homophenylalanine Benzyl ester TosylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of D-Homophenylalanine hydrochloride (1.7 g, 7.93 mmol), benzyl alcohol (7.2 mL, 64.0 mmol) and p-toluenesulfonic acid monohydrate (1.8 g, 9.5 mmol) in benzene (30 mL) was heated at reflux in Dean Stark apparatus during 5 hrs, after which time additional benzene (100 mL) was distilled from reaction mixture. The residue was triturated with diethyl ether, the solid was filtered and dried to give title product (2.93 g).

Workup

  1. temperatureat reflux in Dean Stark apparatus during 5 hrs
  2. distillationafter which time additional benzene (100 mL) was distilled from reaction mixture
  3. customThe residue was triturated with diethyl ether
  4. filtrationthe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-dee368df98c849a39af51c618899546c
Source dataset
uspto-grants-2011_02
Patent number
US07893020B2

Reaction notes

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