Dimethylformamide → HCID 178501117, compound

HRID 1640656Notes

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-dac7f18a0fc84f9fb7f4e2f067b09003
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114846B2

Reaction notes

Loading…