Formaldehyde → HCID 70205561, compound

HRID 651834Notes

Reaction equation

HRID 651834 reaction equation
[O:1]=[C:2]1[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=[O:11])[N:3]1[NH:12][C:13](=[O:32])[C@@H:14]([C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][CH:16]([CH3:18])[CH3:17].[CH2:33]=O>CO.[Pd]>[CH3:33][N:8]1[CH2:9][CH2:10][N:5]2[C:4](=[O:11])[N:3]([NH:12][C:13](=[O:32])[C@@H:14]([C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20]/[CH:21]=[CH:22]/[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:15][CH:16]([CH3:17])[CH3:18])[C:2](=[O:1])[CH:6]2[CH2:7]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 70206206HCID 70206206, compound

Product 1

HCID 70205561HCID 70205561, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.361 g of (E)-N-(1,2,3,5,6,7,8,8a(RS)-octahydro-1,3-dioxoimidazo[1,5-a]pyrazin-2-yl)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-4-methylvaleramide (prepared as described in Example 63) in 10 ml of methanol was treated with 1 ml of 40% aqueous formaldehyde solution and then hydrogenated for 1 hour in the presence of 0.03 g of 10% palladium-on-carbon. The catalyst was removed by filtration and evaporation gave 0.395 g of (E)-N-(1,2,3,5,6,7,8,8a(RS)-octahydro-7-methyl-1,3-dioxoimidazo[1,5-a]pyrazin-2-yl)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-4-methylvaleramide in the form of a clear oil.

Workup

  1. customThe catalyst was removed by filtration and evaporation

Sources & evidence

ORD record
ord-9e89ab4b056d4a6887db5a91f86add33
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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