Benzyl chloroformate → HCID 58430940, compound

HRID 1040481Notes

Reaction equation

HRID 1040481 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1([C:11]2[O:12][C:13]([C:16]([NH2:19])([CH3:18])[CH3:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1COCC1.O>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1([C:11]2[O:12][C:13]([C:16]([NH:19][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])([CH3:18])[CH3:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 67390605HCID 67390605, compound

Product 1

HCID 58430940HCID 58430940, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude {1-[5-(1-amino-1-methyl-ethyl)-furan-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (451 mg, 1.61 mmol) in a mixture of THF (8.0 mL) and water (1.6 mL), was added Li2CO3 (297 mg, 4.02 mmol) followed by benzyl chloroformate (0.57 mL, 4.0 mmol). This was stirred for 2.5 h then diluted with water (50 mL) and extracted EtOAc (3×50 mL). The combined organic layers were dried with Na2SO4 and concentrated to give a red residue. The residue was purified by flash chromatography (silica, 20->40% EtOAc/hexanes) to give 324 mg of the title compound as a yellow oil, m/z 437.64 [M+Na]+.

Workup

  1. extractionextracted EtOAc (3×50 mL)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. concentrationconcentrated
  4. customto give a red residue
  5. customThe residue was purified by flash chromatography (silica, 20->40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a8b19527e17e4ec6be15be530e70e3c9
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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