Hydrochloric Acid → HCID 86722570, compound

HRID 1503614Notes

Reaction equation

HRID 1503614 reaction equation
C(OC(=O)[NH:7][C:8]1([C:11](=[O:18])[NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH2:10][CH2:9]1)(C)(C)C.[ClH:20]>C(Cl)Cl.O1CCOCC1>[ClH:20].[C:8]([CH:10]1[CH2:9][C:8]1([NH2:7])[C:11]([NH:12][CH2:13][C:14]([F:15])([F:16])[F:17])=[O:18])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86722600HCID 86722600, compound

Product 1

HCID 86722570HCID 86722570, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl(1-((2,2,2-trifluoroethyl)carbamoyl)cyclopropyl)carbamate (3.2 g, 11 mmol) in CH2Cl2 (20 mL) was added 4 M HCl in dioxane (20 mL). The solution was stirred for 18 h at ambient temperature. The reaction mixture was concentrated in vacuo and the residue placed in a 60° C. vacuum oven (24 h) to afforded the title compound as an off-white solid (2.3 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 8.77 (bs, 3H), 8.50 (t, J=6.3 Hz, 1H), 3.90 (qd, J=9.7, 6.1 Hz, 2H), 1.52-1.15 (m, 4H); 19F NMR (376 MHz, DMSO-d6) δ −70.54; 13C NMR (101 MHz, DMSO-d6) δ 175.33, 132.46 (q, J=280.8 Hz), 45.13 (q, J=34.34 Hz), 40.06, 17.57.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customplaced in a 60° C.
  3. customvacuum oven (24 h)

Sources & evidence

ORD record
ord-c36bba1e6ff946709784ec5835e8a55d
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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