Hydrochloric Acid → tert-Butyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbonyl)methylamino]acetate

HRID 17493Notes

Reaction equation

HRID 17493 reaction equation
C[Al](C)C.Cl.[C:6]([O:10][C:11](=[O:15])[CH2:12][NH:13][CH3:14])([CH3:9])([CH3:8])[CH3:7].[C:16]([C:18]1[C:23]2[N:24]=[C:25]([C:27](OCC)=[O:28])[O:26][C:22]=2[C:21]([F:32])=[C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]=1[CH3:39])#[N:17].Cl>ClCCl>[C:16]([C:18]1[C:23]2[N:24]=[C:25]([C:27]([CH2:14][NH:13][CH2:12][C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:15])=[O:28])[O:26][C:22]=2[C:21]([F:32])=[C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]=1[CH3:39])#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

Product 1

HCID 86630857tert-Butyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbonyl)methylamino]acetateYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 4.50 ml, 4.63 mmol) was dropwise added at room temperature to a dichloromethane (6 ml) solution of N-methylglycine tert-butyl ester hydrochloride (840 mg, 4.63 mmol), followed by stirring for 25 hours. Subsequently, a dichloromethane (4 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (500 mg, 1.54 mmol) was dropwise added, followed by stirring for 23 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain the entitled compound (569 mg, 87%) as a white solid.

Workup

  1. stirringby stirring for 23 hours
  2. additionwas added to the reaction liquid
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature
  5. customthe reaction liquid
  6. extractionwas extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. washwashed in diethyl ether

Sources & evidence

ORD record
ord-abec07b406974cb0a332db3ca8eef204
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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