(S)-1-(3-Chlorophenyl)ethane-1,2-diol → (s)-(2-(3-Chlorophenyl)-2-hydroxyethyl)oxocarboxamide

HRID 365587

Reaction equation

HRID 365587 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([O:14]C(=O)N)[CH2:9][C:10]([N:12]=[O:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.ClC1C=C([C@H](O)CO)C=CC=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:14])[CH2:9][C:10]([N:12]=[O:13])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10130180(S)-1-(3-Chlorophenyl)ethane-1,2-diolHCID 131721943(s)-(2-(3-Chlorophenyl)-2-carbamoyloxyethyl)oxocarboxamide

Product 1

HCID 131721942(s)-(2-(3-Chlorophenyl)-2-hydroxyethyl)oxocarboxamideYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-(2-(3-Chlorophenyl)-2-carbamoyloxyethyl)oxocarboxamide (1.36 g, yield 25%, m.p. 117-119° C., [α]D =12.88 (c=2.30, MeOH) was prepared using the same synthetic method described in Example 20, except (S)-1-m-chlorophenyl-1,2-ethanediol was used instead of (DL)-1-m-chlorophenyl-1,2-ethanediol.

Sources & evidence

ORD record
ord-6cfca9cd125a4350a3f7dbb8723965ae
Source dataset
uspto-grants-2000_10
Patent number
US06127412

Linked notes

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