Oxalyl chloride → HCID 69877481, compound

HRID 1860045Notes

Reaction equation

HRID 1860045 reaction equation
[CH:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH2:21]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([Li])CCC>CCCCCC>[CH2:21]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[N:29]1[C:10](=[O:12])[CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:14][CH:13]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 1371314-Isopropylphenoxyacetic acidHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 69877481HCID 69877481, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a similar manner to that described in Refernce example 29(a), a reaction was carried out using 4-isopropylphenoxyacetic acid (14.1 g), oxalyl chloride (15.8 ml), (R)-4-benzyloxazolidine-2-one (11.7 g) and a solution of n-butyl lithium in hexane (1.61N, 45.0 ml) and the reaction mixture was treated to afford the desired compound (18.6 g) as colorless crystals.

Sources & evidence

ORD record
ord-56d86ce9013e434eb06c9136cb050085
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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