Hydrochloric Acid → HCID 86722570, compound

HRID 1503787Notes

Reaction equation

HRID 1503787 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][NH:4][C:5]([C:7]1([NH:10]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1)=[O:6].[ClH:20]>C(Cl)Cl.O1CCOCC1>[ClH:20].[C:7]([CH:9]1[CH2:8][C:7]1([NH2:10])[C:5]([NH:4][CH2:3][C:2]([F:1])([F:18])[F:19])=[O:6])([CH3:9])([CH3:8])[CH3:5]

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-a887ee30e36b4c8b9da4d57ae3e82a85
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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