Methyl iodide → HCID 66622747, compound

HRID 416367Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH2:18][O:19][CH2:20][CH:21]1[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]1)[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:28])[N:7]([CH:8]([CH2:18][O:19][CH2:20][CH:21]1[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]1)[CH2:9][O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:31])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [2-Benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-ethyl]-carbamic acid tert-butyl ester (1.26 g, 3.18 mmol) in DMF (10 mL) was added sodium hydride (60%, 0.19 g, 4.78 mmol) at 0° C. in one portion. The reaction was stirred at 0° C. for 0.5 h then MeI (1.36 g, 9.56 mmol) was added. The reaction mixture was then stirred at 0° C. for 3 h at which time the LC-MS showed the reaction was complete. The reaction was quenched with saturated aq. NH4Cl solution and extracted with EtOAc (2×100 mL). The organic layer was then washed with water, brine and dried over Na2SO4. The organic layers were concentrated to give [2-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-ethyl]-methyl-carbamic acid tert-butyl ester (1.25 g, 96%). LRMS (M-Boc+H+) m/z 310.1.

Workup

stirringThe reaction mixture was then stirred at 0° C. for 3 h at which time the LC-MS
customThe reaction was quenched with saturated aq. NH4Cl solution
extractionextracted with EtOAc (2×100 mL)
washThe organic layer was then washed with water, brine
dry with materialdried over Na2SO4
concentrationThe organic layers were concentrated

Sources & evidence

ORD record: ord-15fda8c72ec648e48bc4f4d8c321ab7d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088793B2

Reaction notes

Loading…