Formaldehyde → HCID 70203733, compound

HRID 651831Notes

Reaction equation

HRID 651831 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:19]([NH:21][N:22]1[C:26](=[O:27])[C:25]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[NH:24][C:23]1=[O:33])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:38]=O.[H][H]>[Pd].CO>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:19]([NH:21][N:22]1[C:26](=[O:27])[C:25]2([CH2:32][CH2:31][N:30]([CH3:38])[CH2:29][CH2:28]2)[NH:24][C:23]1=[O:33])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 70203736HCID 70203736, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70203733HCID 70203733, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.403 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide, 0.145 ml of 38% aqueous formaldehyde solution and 0.093 g of 10% palladium-on-charcoal catalyst in 4 ml of methanol was shaken in a hydrogen atmosphere for 2 days. The catalyst was filtered off and the methanol evaporated. The residue was re-evaporated from toluene and the solid obtained triturated with diethyl ether. There was obtained 0.348 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-(8-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl)valeramide in the form of a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe methanol evaporated
  3. customThe residue was re-evaporated from toluene
  4. customthe solid obtained
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-7eb5ef0834a242cdbdcfcf3c0c029c1a
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

Loading…