1,2-Dichloroethane → HCID 69515673, compound

HRID 1297238Notes

Reaction equation

HRID 1297238 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:16]([OH:18])=O)[CH2:12][CH:11]1[CH:13]([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:25]C=2C=1.CN1CCOCC1.C(Cl)CCl>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([C:16](=[O:18])[NH2:25])[CH2:12][CH:11]1[CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 22182729HCID 22182729, compound

Product 1

HCID 69515673HCID 69515673, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(tert-butoxycarbonylamino-methyl)-2-isopropyl-cyclopropanecarboxylic acid (6.4 g, 24.9 mmol) in dry THF (190 mL) was added HOBt (4.7 g, 34.8 mmol), NMM (3.83 mL, 34.8 mmol) and EDC (6.7 g, 34.8 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours and quenched with concentrated ammonium hydroxide (16 mL). The reaction mixture was stirred at room temperature overnight. Excess of solvent was removed in vacuo and the residue was dissolved in EtOAc (200 mL). The organic layer was washed with 1N HCl, aqueous NaHCO3, brine and dried over Na2SO4. Evaporation of excess of solvent gave 6.4 g (100%) of (1-carbamoyl-2-isopropyl-cyclopropylmethyl)-carbamic acid tert-butyl ester as a colorless oil: 1H NMR (300 MHz, CD3OD) δ 0.62 (m, 1H), 1.00 (d, 3H), 1.05 (d, 3H), 1.25 (m, 3H), 1.45 (s, 9H), 3.05 (dd, 1H), 3.80 (dd, 1H), 6.70 (m, 1H); MS (APCI) m/z 257 [M+H]+

Workup

  1. customquenched with concentrated ammonium hydroxide (16 mL)
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customExcess of solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc (200 mL)
  5. washThe organic layer was washed with 1N HCl, aqueous NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of excess of solvent

Sources & evidence

ORD record
ord-422a9679d7a64f7eb308ca57004d430f
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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