Dichloromethane → tert-butyl N-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-beta-alaninate

HRID 17564Notes

Reaction equation

HRID 17564 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.ClCCl.Cl[C:25]1[O:26][C:27]2[C:28](=[C:30]([C:42]#[N:43])[C:31]([CH3:41])=[C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:33]=2[F:34])[N:29]=1>C(OCC)(=O)C>[C:42]([C:30]1[C:28]2[N:29]=[C:25]([NH:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[O:26][C:27]=2[C:33]([F:34])=[C:32]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:31]=1[CH3:41])#[N:43]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68585188tert-butyl N-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-beta-alaninateYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

With cooling with ice, tert-butyl 3-aminopropionate hydrochloride (230 mg, 1.26 mmol) and diisopropylethylamine (430 μl, 2.53 mmol) were added to a dichloromethane (10 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (302 mg, 1.05 mmol), followed by stirring at room temperature for 1 hour. The reaction liquid was cooled to room temperature, then ethyl acetate was added, and followed by washing with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1→1:1, v/v) to obtain the entitled compound (402 mg, 97%) as a white solid.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. washby washing with saturated brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe insoluble matter was separated by filtration
  6. customthe residue obtained by concentration
  7. customwas purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-4721cad7db674ea2bc7b4737ac727b8a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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