1,2-Dichloroethane → HCID 59382986, compound

HRID 2355455Notes

Reaction equation

HRID 2355455 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]([F:25])([F:24])[CH2:22][NH2:23].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[F:20][C:21]([F:25])([F:24])[CH2:22][NH:23][C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 757711-HydroxybenzotriazoleHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Product 1

HCID 59382986HCID 59382986, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2S)-2-tert-butoxycarbonylamino-3-cyclohexyl-propionic acid (2.98 g, 11 mmol), 2,2,2-trifluoroethylamine (1.35 g, 10 mmol), EDC (2.87 g, 15 mmol), HOBt (2.03 g, 15 mmol) and NMM (5.05 g, 50 mmol) in 100 mL of CH2Cl2 was stirred overnight. The mixture was poured into water (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, and evaporated to give the residue. The residue was purified by silica chromatography to give tert-butyl (S)-1-(2,2,2-trifluoroethylcarbamoyl)-2-cyclohexylethylcarbamate (2.8 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 0.90 (m, 2H), 1.25 (m, 4H), 1.44 (s, 9H), 1.68 (m, 7H), 3.89 (m, 1H), 4.16 (brs, 1H), 4.82 (brs, 1H), 6.78 (brs, 1H).

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give the residue
  6. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-759932ce61164d2e9a65a4b0ec16f471
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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