Hydrochloric Acid → HCID 68831074, compound

HRID 747787Notes

Reaction equation

HRID 747787 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38]([C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)#[N:39].Cl>CN(C)C=O>[CH2:1]([N:8]([C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:44](=[O:45])[C:43]1[CH:47]=[CH:48][C:40]([C:38]#[N:39])=[CH:41][CH:42]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 53773903HCID 53773903, compound

Product 1

HCID 68831074HCID 68831074, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

190 mg (0.47 mmol) of benzyl 3-(3R)-benzylamino-4-(3-cyanophenoxy)butyrate and 153 mg of triethylamine were stirred in 5 ml of dimethylformamide, and 70 mg (0.47 mmol) of 4-cyanobenzoyl chloride was added thereto under cooling with ice and stirred for 3 hours. 1 N hydrochloric acid was added thereto, followed by extraction with ethyl acetate. The extract was washed with 1 N sodium hydroxide and saturated saline and dried over magnesium sulfate anhydride, and the solvent was distilled off and the residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with 1 N sodium hydroxide and saturated saline
  4. dry with materialdried over magnesium sulfate anhydride
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-07d3fef3e6164a1b95538d67c1ce9197
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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