Isopropanol → HCID 58457049, compound

HRID 245558Notes

Reaction equation

HRID 245558 reaction equation
[C:1](=[O:21])([O:7][C:8]1[C:12]2[CH:13]=[C:14]([CH:19]=O)[C:15](F)=[C:16]([F:17])[C:11]=2[O:10][N:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24].[CH3:31][CH:32]([OH:34])[CH3:33]>>[C:1](=[O:21])([O:7][C:8]1[C:12]2[CH:13]=[C:14]3[C:15](=[C:16]([F:17])[C:11]=2[O:10][N:9]=1)[N:9]1[CH2:31][C@@H:32]([CH3:33])[O:34][C@@H:12]([CH3:11])[C@@H:8]1[C:28]1([C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22][C:29]1=[O:30])[CH2:19]3)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 6211Barbituric AcidHCID 87368680HCID 87368680, compound2×

Product 1

HCID 58457049HCID 58457049, compound

Conditions

Temperature
80 °C

Procedure

To a stirred solution of tert-butyl 6,7-difluoro-5-formyl-1,2-benzisoxazol-3-yl carbonate Intermediate 531 (175 mg, 0.44 mmol) in dry IPA (10 mL) was added barbituric acid (8 mg, 0.062 mmol), and the solution heated around 80° C. for 12 h. Solvents were evaporated and the residue was purified over a silica gel column to give product as a white solid. Yield: 40 mg (18%).

Workup

  1. customSolvents were evaporated
  2. customthe residue was purified over a silica gel column
  3. customto give product as a white solid

Sources & evidence

ORD record
ord-b4996f2a482647c9b66f92729cc38931
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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