Formic Acid → HCID 67307837, compound

HRID 2061620Notes

Reaction equation

HRID 2061620 reaction equation
O[CH:2]1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:5]([CH2:17][C:18]#[CH:19])[C:4]([CH3:21])([CH3:20])[CH2:3]1.C(O)=[O:23]>>[CH3:20][C:4]1([CH3:21])[N:5]2[N:6]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH:2]([CH2:19][C:18](=[O:23])[CH2:17]2)[CH2:3]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86640527HCID 86640527, compound

Product 1

HCID 67307837HCID 67307837, compoundYield 18%

Procedure

A stirred solution of 105 (2.5 g, 8.6 mmol) in formic acid (10 mL) was heated at 100° C. for 5 h. After complete consumption of 105 (as monitored by TLC), formic acid was evaporated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with saturated with NaHCO3 solution (2×50 mL), water (50 mL) and brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified through preparative HPLC to afford 106 (0.52 g, 18%). 1H NMR (CDCl3) δ 7.30-7.40 (m, 5H), 5.25 (s, 2H), 3.62 (m, 1H), 2.76 (m, 1H), 2.42 (m, 1H), 2.20 (m, 1H), 2.09 (s, 1H), 1.65 (m, 1H), 1.22 (s, 3H), 1.13 (s, 3H).

Workup

  1. customAfter complete consumption of 105 (as monitored by TLC), formic acid
  2. customwas evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with saturated with NaHCO3 solution (2×50 mL), water (50 mL) and brine solution (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude compound which
  8. customwas purified through preparative HPLC

Sources & evidence

ORD record
ord-0b5ccf24627f4c74a66edcb09dc37e06
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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