tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → HCID 67970625, compound

HRID 1500229Notes

Reaction equation

CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH:16]([Mg]Cl)([CH3:18])[CH3:17].C1([Mg]Br)CC1>C1COCC1>[CH:16]1([C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of tert-butyl N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (2,455.3 g, 11.25 mol) in THF (9.0 L) is added 2.0M isopropylmagnesium chloride in THF (5.34 L, 10.69 mol) at −30° C. via an addition funnel over a period of 60 min such that the internal temperature does not exceed 0° C. The mixture is then warmed slowly to 10° C. and 0.5M cyclopropylmagnesium bromide in THF (27.0 L, 13.50 mol) is added via an addition funnel over a period of 1 h. The mixture is stirred at room temp 24 h. The mixture is cooled to 0° C. and quenched with 1.0M HCl to pH 5-6, then warmed to room temp and extracted with EtOAc (12 L and 10 L). The combined organic phase is washed successively with water (10 L) and brine (8 L), dried over Na2SO4, and filtered. The filtrate is evaporated under reduced pressure to afford 2.24 kg (100% yield) of the title compound as a light yellow oil which is used directly for the next step.

Workup

customdoes not exceed 0° C
temperatureThe mixture is cooled to 0° C.
customquenched with 1.0M HCl to pH 5-6
temperaturewarmed to room temp
extractionextracted with EtOAc (12 L and 10 L)
washThe combined organic phase is washed successively with water (10 L) and brine (8 L)
dry with materialdried over Na2SO4
filtrationfiltered
customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record: ord-366de8616ace4c80a88893dbf8add79d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206139B2

Reaction notes

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