Diethyl (methanesulfonylmethyl)phosphonate → HCID 178453929, compound

HRID 711944Notes

Reaction equation

CC(C)([O-])C.[K+].[CH3:7][S:8]([CH2:11]P(=O)(OCC)OCC)(=[O:10])=[O:9].[CH:20]([C@H:22]1[CH2:27][CH2:26][C@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH2:23]1)=O>O1CCCC1>[CH3:7][S:8]([CH:11]=[CH:20][C@H:22]1[CH2:23][CH2:24][C@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:26][CH2:27]1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.0 M potassium tert-butoxide in tetrahydrofuran (THF) (1.0 mL, 1.0 mmol) was added diethyl [(methylsulfonyl)methyl]phosphonate (0.21 g, 0.92 mmol) dropwise at 0° C. and the resulting mixture was stirred at 0° C. for 1 h. A solution of tert-butyl (trans-4-formylcyclohexyl)carbamate (0.15 g, 0.66 mmol) in tetrahydrofuran (4.6 mL) was added dropwise, then cooling bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with water, concentrated and purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (0.14 g, 70%) as a mixture of E- and Z-isomers. LCMS calculated for C14H25NO4SNa (M+Na)+: m/z=326.2. Found: 326.1.

Workup

temperaturecooling bath
customwas removed
stirringthe mixture was stirred at room temperature for 1 h
additionThe reaction mixture was diluted with EtOAc
washwashed with water
concentrationconcentrated
custompurified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-7d2bca60130444e595463a4605b1d8e4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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