tert-Butanol → tert-Butyl 2-chloro-2-oxoacetate

HRID 2363263Notes

Reaction equation

HRID 2363263 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[C:7]([OH:11])([CH3:10])([CH3:9])[CH3:8]>CCOCC>[C:7]([O:11][C:1](=[O:5])[C:2]([Cl:4])=[O:3])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 65578Oxalyl chloride

Product 1

HCID 11126621tert-Butyl 2-chloro-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Oxalyl chloride (12.4 μL. 0.1 mmol) and t-butyl alcohol (13.1 μL) were combined in ether (0.3 mL) under nitrogen at 0° C. The resulting mixture was stirred for 30 minutes at room temperature. The solvent was evaporated under vacuum to form chloro-oxo-acetic acid t-butyl ester, which was then dissolved in DCM (0.7 mL) and combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methylpentanoic acid ethyl ester (33.4 mg, 98 μmol). Et3N (43.6 μL,) at 0° C. was added and the resulting mixture was stirred for 30 minutes at room temperature. The solvent were evaporated and the residue was dissolved in 1:1 TFA:DCM and stirred for 1 hour. AcOH was added and the product was purified by preparative HPLC to yield the title compound (7 mg, purity 95%). MS m/z [M+H]+ calc'd for C23H27NO6, 414.18. found 414.4.

Workup

  1. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-428f1a2a54d34dc483e64f8e11f33441
Source dataset
uspto-grants-2014_04
Patent number
US08691868B2

Reaction notes

Loading…