Methyl chloroformate → 4-(tert-Butyl)-2-(2-cyanopropan-2-yl)phenyl methyl carbonate

HRID 1617298Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:27]([O:29][CH3:30])=[O:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:27](=[O:28])([O:29][CH3:30])[O:16][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][C:9]=1[C:11]([C:12]#[N:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of compound 15 (126.6 g, 0.564 mol), DMAP (6.0 g) and DIEA (188 g, 1.46 mol) in anhydrous DCM (1500 mL) was added dropwise methyl chloroformate (110 g, 1.17 mol) in anhydrous DCM (300 mL) at 0° C. within 2 hours. After stirring for 12 hours at 0° C., ice-water (1.5 L) was added and the mixture was stirred at 0° C. for 30 minutes. The organic layer was separated and washed with 1 N HCl, water, and brine. The DCM solution was dried over MgSO4 and concentrated in vacuo to give compound 16 as a yellow solid. 1H NMR (DMSO-d6; 400 MHz) δ 7.47 (m), δ 7.39 (d), δ 7.24 (d), δ 3.84 (s), δ 1.71 (s), δ 1.30 (s).

Workup

stirringthe mixture was stirred at 0° C. for 30 minutes
customThe organic layer was separated
washwashed with 1 N HCl, water, and brine
dry with materialThe DCM solution was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a6099163de2d459e8900f9b760562367
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765957B2

Reaction notes

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