Ethyl chloroformate → [1-(4-Benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester

HRID 1833137Notes

Reaction equation

HRID 1833137 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19](OC)[CH:18]=2)=[CH:11][C:10]=1[O:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:41]([O:43][CH2:44][CH3:45])=[O:42].C(OCC)(=O)C.CCCCCC>O1CCCC1.O.C(OCC)C>[CH2:44]([O:43][C:41](=[O:42])[N:25]([CH:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:32][CH3:33])[CH:11]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:26][CH:27]([O:28][CH3:29])[O:30][CH3:31])[CH3:45]

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22048300[1-(4-Benzyloxy-3-methoxy-phenyl)-2-(3-methoxyphenyl)-ethyl]-(2,2-dimethoxy-ethyl)-amine

Product 1

HCID 69550811[1-(4-Benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl esterYield 70.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [1-(4-benzyloxy-3-methoxy-phenyl)-2-(3-methoxy-phenyl)-ethyl]-(2,2-dimethoxy-ethyl)-amine (10.46 g, 20 mmol) in tetrahydrofuran (40 mL) and water (20 mL) was added potassium carbonate (5 g, 36 mmol) and ethyl chloroformate (1.91 mL, 20 mmol) dropwise. The mixture was stirred for 1 h at room temperature. The mixture was diluted with diethyl ether (100 mL), and the organic layer was separated. The aqueous phase was extracted with ethyl acetate (3×100 mL) and the combined extracts were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 20% ethyl acetate/hexane) afforded [1-(4-benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester (7 g, 67% yield in three steps) as a colorless oil.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
  3. washthe combined extracts were washed with saturated aqueous sodium chloride solution (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4b7e633555a4bac8695ae2693a52845
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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