2-Chloromandelic acid → (S(R*,R*))-2-amino-1-phenylpropane-1,3-diol

HRID 130611

Reaction equation

HRID 130611 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[C:3]([OH:5])=[O:4].[C:13]1([C@H:19]([OH:24])[C@@H:20]([NH2:23])[CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OC(=O)C)C.O>[OH:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[C:3]([O-:5])=[O:4].[C:13]1([C@H:19]([OH:24])[C@@H:20]([NH2:23])[CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 977202-Chloromandelic acidHCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diol

Product 2

HCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diolHCID 6922873(S)-(+)-2-hydroxy-2-(2-chlorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(The compound of the general formula (II)—wherein R1 is a hydroxy-methyl group, R2 is a phenyl group, R3 is a hydroxy group) Racemic 2-hydroxy-2-(2-chlorophenyl)acetic acid (20.0 g 107 mmol) was dissolved in 60 cm3 of ethylacetate saturated with water and (1S, 2S)-(+)-1-phenyl-2-amino-1,3-propane-diol (18.0 g 107.5 mmol) was added thereto and then the mixture was seed by a salt formed from (S)-(+)-2-hydroxy-2-(2-chlorophenyl)acetate and (1S, 2S)-(+)-1-phenyl 2-amino-1,3-propane-diol at room temperature.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-905f9881af514c839e3efb384d85a9ad
Source dataset
uspto-grants-2008_06
Patent number
US07381835B2

Linked notes

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