Formic Acid → HCID 69956033, compound

HRID 2293306Notes

Reaction equation

HRID 2293306 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]2[CH:11]([CH3:22])[NH:12][CH:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH:7]2[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].[CH:24](O)=O.C=O>[OH-].[Na+]>[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]2[CH:11]([CH3:22])[N:12]([CH3:24])[CH:13]([C:14]3[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=3)[CH:7]2[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 69954596HCID 69954596, compound

Product 1

HCID 69956033HCID 69956033, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.84 g of (1RS,3SR,3aRS,6aSR)-4-(5-butyl-3-methyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile, 85% formic acid (4.9 g, 90 mmol) and 35% formalin solution (2.6 g, 30 mmol) were heated to 100° C. for 5.5 hours. After cooling 1N NaOH (50 ml) was added and the mixture was extracted four times with dichloromethane. The organic phase was concentrated and the residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine). 2.52 g of (1RS,3SR,3aRS,6aSR)-4-(5-butyl-2,3-dimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile (85%) were isolated as a colourless oil. EI-MS: 325 (M+, 8); 310 (95); 223 (10); 183 (24); 171 (40); 157 (10); 143 (9); 70 (15); 56 (17); 43 (100).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted four times with dichloromethane
  3. concentrationThe organic phase was concentrated
  4. customthe residue was separated chromatographically (hexane/ethyl acetate 3:1+1% triethylamine)

Sources & evidence

ORD record
ord-6e8f14d6e6da4f598e5361d44d09f208
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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