Formaldehyde → HCID 60077775, compound

HRID 2084544Notes

Reaction equation

HRID 2084544 reaction equation
C=O.C(O[C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:39])[C@@H:26]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=O)C1C=CC=CC=1>CO.C(OCC)(=O)C>[C:35]([O:34][C:32](=[O:33])[NH:31][C@H:26]([C:25](=[O:39])[C:22]1[CH:21]=[CH:20][C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH3:11])[CH2:18][CH2:17]2)=[CH:24][CH:23]=1)[C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:36])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 69864498HCID 69864498, compound

Product 1

HCID 60077775HCID 60077775, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Formaldehyde (37% wt. % solution in H2O, 0.5 mL) was added to a solution of 4-[4-(2(S)-tert-Butoxycarbonylamino-3,3-dimethylbutyryl)-phenyl]-piperazine-1-carboxylic acid benzyl ester in methanol (3 mL) and ethyl acetate (1 mL). The mixture was degassed and 10% palladium on charcoal (20 mg) was added. Hydrogen gas was bubbled through the suspension for 15 minutes when a balloon containing hydrogen was introduced to the reaction. After 18 hours, the catalyst was removed by filtration and the solvents were removed in vacuo to give a yellow oil which was used without further purification (0.15 g, 100% crude).

Workup

  1. customThe mixture was degassed
  2. addition10% palladium on charcoal (20 mg) was added
  3. customHydrogen gas was bubbled through the suspension for 15 minutes when a balloon
  4. additioncontaining hydrogen
  5. additionwas introduced to the reaction
  6. customthe catalyst was removed by filtration
  7. customthe solvents were removed in vacuo
  8. customto give a yellow oil which
  9. customwas used without further purification (0.15 g, 100% crude)

Sources & evidence

ORD record
ord-db210f57bce540f6a99a2106ef130451
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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