Triethylamine → HCID 59603843, compound

HRID 2046400Notes

Reaction equation

HRID 2046400 reaction equation
FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[F:15][C:16]1([F:24])[CH2:21][CH2:20][CH2:19][C@H:18]([NH3+:22])[C@H:17]1[NH3+:23].C(N(CC)CC)C.[O:32](C(OC(C)(C)C)=O)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=O>ClCCl>[C:36]([O:35][C:33](=[O:32])[NH:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C:16]([F:24])([F:15])[C@@H:17]1[NH2:23])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86660884HCID 86660884, compound

Product 1

HCID 59603843HCID 59603843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1S,2R)-3,3-difluorocyclohexane-1,2-diaminium bis(trifluoroacetate) (7.5 g, 19.8 mmol) in dichloromethane (100 mL) was added triethylamine (11.1 mL, 79.0 mmol) followed by BOC2O (5.52 mL, 23.8 mmol). The reaction was stirred for 10 hr at ambient temperature. Concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (CDCl3, 500 MHz) 4.76 (br s, 1H); 3.39 (m, 1H); 2.71-2.64 (m, 1H); 2.2-2.1 (m, 2H); 1.7-1.59 (m, 2H); 1.56-1.51 (m, 2H); 1.45 (s, 9H); 1.29-1.21 (m, 2H). 19F NMR (CDCl3, 564 MHz) −100.4-−100.9 (d, 1F); −114.35-−114.87 (d, 1F).

Workup

  1. concentrationConcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f02264c5ad5e4e399827f1b0eadccbc4
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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