Triethylamine → HCID 57563477, compound

HRID 1726320Notes

Reaction equation

HRID 1726320 reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][CH:4]([NH:12][C:13]([C:15]1[CH:20]=[C:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][C:16]=1[CH2:29][CH2:30][C:31](O)=[O:32])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.C([N:37](CC)CC)C.ClC(OCC)=O.O.N>O1CCCC1.O>[O:22]([CH2:21][C:19]1[CH:18]=[CH:17][C:16]([CH2:29][CH2:30][C:31]([NH2:37])=[O:32])=[C:15]([C:13](=[O:14])[NH:12][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[CH2:3][CH:2]([CH3:34])[CH3:1])[CH:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12896473Azane;hydrateHCID 23016797HCID 23016797, compound

Product 1

HCID 57563477HCID 57563477, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 6(40) (150 mg) in tetrahydrofuran (2 ml) were added triethylamine (0.068 ml) and ethyl chloroformate (0.037 ml). The mixture was stirred at room temperature for 30 minutes under an atmosphere of argon. To the reaction mixture was added ammonia water and the mixture was stirred for 10 minutes. To the reaction mixture was added water and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with n-hexane-ethyl acetate to give the title compound (119 mg) having the following physical data.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, water
  4. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washThe residue was washed with n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-8470f4052b0e4181abb81a50f7c32d3a
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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