Dimethylformamide → HCID 178501117, compound

HRID 1993256Notes

Reaction equation

ClS([N:5]=C=O)(=O)=O.[CH3:8][O:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18](O)=O)[CH2:14][CH2:13]1)=[O:11].CN(C=O)C>C(Cl)Cl>[C:18]([C@H:15]1[CH2:16][CH2:17][C@H:12]([C:10]([O:9][CH3:8])=[O:11])[CH2:13][CH2:14]1)#[N:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Chlorosulfonyl isocyanate (1.0 mL, 0.012 mol) was added to a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (2.00 g, 0.0107 mol) in DCM cooled to 0° C. The resulting solution was heated at reflux for 15 minutes and then cooled 0° C. and treated dropwise with DMF. The mixture was stirred at room temperature overnight then poured onto ice water and the organic phase separated and washed with a saturated solution of sodium bicarbonate. The solvent was removed in vacuo and the crude material was taken up in ethyl acetate, washed with 1N aq. NaOH (10 mL) and the ethyl acetate removed in vacuo. The resulting crude product was used in subsequent steps without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36-1.70 (4 H, m), 2.01-2.18 (4 H, m), 2.24-2.54 (2 H, m) and 3.68 (3 H, s).

Workup

temperatureThe resulting solution was heated
temperatureat reflux for 15 minutes
temperaturecooled 0° C.
additionthen poured onto ice water
customthe organic phase separated
washwashed with a saturated solution of sodium bicarbonate
customThe solvent was removed in vacuo
washwashed with 1N aq. NaOH (10 mL)
customthe ethyl acetate removed in vacuo
customThe resulting crude product was used in subsequent steps without further purification

Sources & evidence

ORD record: ord-0e3d93b191c14e5798923bae641b2749
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07651687B2

Reaction notes

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