Formaldehyde → Formate

HRID 418325Notes

Reaction equation

HRID 418325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:26])[NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]2)[CH:11]=1)=[O:7].[CH2:32]=[O:33]>C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:26])[NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][N:22]([CH3:32])[CH2:21]2)[CH:11]=1)=[O:7].[CH:31]([O-:30])=[O:33]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 25057408HCID 25057408, compound

Product 2

HCID 283FormateYield 28%HCID 25057932HCID 25057932, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Compound 33 (80 mg, 0.188 mmol), (Example 8), was dissolved in formic acid (0.5 mL) and formaldehyde (0.5 mL, 37% aqueous solution) was added. The resulting mixture was heated at 70° C. overnight. The solvents were evaporated and the product was purified by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (23 mg, 28% yield), MS analysis electrospray, 440 (M+H).

Workup

  1. customThe solvents were evaporated
  2. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-58b00b0d2cad4db8b5807004fa11bbab
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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