2-Chlorobenzoxazole → HCID 57513847, compound

HRID 2368445Notes

Reaction equation

HRID 2368445 reaction equation
Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5].Cl[C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1>C(Cl)Cl>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[N:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[C:4]([O:3][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 57513847HCID 57513847, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.66 G (S)-pyrrolidine-2-carboxylic acid methyl ester, hydrochloride salt and 1.15 mL of 2-chlorobenzoxazole in 6 mL CH2Cl2 was subjected to microwave heating at 120° C. for 0.5 h. Solvent was evaporated. Purification by chromatography (SiO2, EtOAc/heptane) provided 2.283 g (93% yield) of (S)-1-benzooxazol-2-yl-pyrrolidine-2-carboxylic acid, methyl ester as a waxy white solid, m/z 247.16 (MH+). A mixture of 2.0 g of (S)-1-benzooxazol-2-yl-pyrrolidine-2-carboxylic acid, methyl ester and 1.02 G LiOH H2O in 15 mL MeOH and 15 mL water was stirred overnight at room temperature. The reaction was acidified with 1N HCl, was extracted three times with MeOH/CH2Cl2, was dried over Na2SO4 and was evaporated to provide the title compound. m/z 233.17 (MH+).

Workup

  1. customSolvent was evaporated
  2. customPurification by chromatography (SiO2, EtOAc/heptane)

Sources & evidence

ORD record
ord-4b747c28757f423aa831b823928ee9e9
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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