Tetrahydrofuran → HCID 67421846, compound

HRID 1897420Notes

Reaction equation

HRID 1897420 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][N:14]2[CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:10][C:9]=1[O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:7].C1C[O:33]CC1>>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH2:5].[F:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][C:8]=2[C:6]([OH:7])=[O:33])[N:14]([CH2:17][CH:18]([CH3:19])[CH3:20])[N:13]=[CH:12]3)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 57484110HCID 57484110, compound

Product 1

HCID 67421846HCID 67421846, compoundYield 30%

Conditions

Temperature
65 °C

Procedure

Compound 11g-10 (0.05 g, 0.12 mmol), prepared as described in Example 59, was treated with 6 equivalents of BH3 in THF (1 M solution) and stirred at 65° C. for 6 hours and then at room temperature for 14 hours. The solvent was removed by evaporation, and the residue was purified on by preparative TLC using 1:1 hexane/ethyl acetate and 5% triethylamine to provide 0.014 g (30% yield) of product. MH+ observed: 385.

Workup

  1. waitat room temperature for 14 hours
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified on by preparative TLC

Sources & evidence

ORD record
ord-844fc5a8c90e4f14a999310ba22a54a4
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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