Methyl chloroglyoxylate → Methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate

HRID 1366612Notes

Reaction equation

[CH3:1][C:2]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)C(C)C)(C)C.Cl[C:27](=[O:32])[C:28]([O:30][CH3:31])=[O:29]>C1COCC1.CCOC(C)=O>[CH3:8][C:2]([N:9]([C:27](=[O:32])[C:28]([O:30][CH3:31])=[O:29])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH3:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 3-methyl-3-[(phenylmethyl)amino]butanoate (5.5853 g, 25.24 mmol) in THF (125 mL) was added N,N-diisopropylethylamine (6.6 mL, 37.89 mmol). The solution was cooled to 0° C., and methyl chloro(oxo)acetate (2.55 mL, 27.73 mmol) was added dropwise. The mixture was then allowed to stir and warm to room temperature overnight. The mixture was diluted with EtOAc (200 mL) and washed with 1 N aq. HCl (100 mL), followed by sat. aq. NaHCO3 (100 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was crystallized from EtOAc—hexanes to give a white solid that was collected by vacuum filtration and washed with hexanes. The resulting methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate (7.0709 g, 91%) was obtained as a white solid. LCMS: (M+H)+: 308.1.

Workup

temperaturewarm to room temperature overnight
washwashed with 1 N aq. HCl (100 mL)
dry with materialThe organic phase was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was crystallized from EtOAc—hexanes
customto give a white solid
filtrationthat was collected by vacuum filtration
washwashed with hexanes

Sources & evidence

ORD record: ord-5cfe61130e5c4ee7b0fd0dab662b97e8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

Loading…