HCID 67753987, compound → HCID 67753956, compound

HRID 355679Notes

Reaction equation

HRID 355679 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[CH:17][C:18]1[S:19][C:20]([CH2:23][CH:24]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][NH:25]2)=[CH:21][CH:22]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[NH3:11].[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[S:19][C:20]([CH2:23][CH:24]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][NH:25]2)=[CH:21][CH:22]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 67753987HCID 67753987, compound

Product 2

HCID 222AmmoniaHCID 67753956HCID 67753956, compoundYield 11.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In an atmosphere of argon, 30 ml of methanol solution containing 2.03 g of the compound of Example 39 was mixed with 500 mg of palladium black and stirred for 3 days to effect hydrogenation. Then, 1 g of activated carbon was added and the mixture was filtered. The filtrate was evaporated under reduced pressure and then the residue was subjected to silica gel column chromatography and elution was carried out with a series of mixed solutions of chloroform:methanol=40:1 and 20:1 and chloroform:methanol:concentrated aqueous ammonia=300:10:1 and 100:10:1 in that order to obtain 120 mg of methyl 2-benzyloxycarbonylamino-3-[5-(1-hexahydroazepinylmethyl)-2-thienyl]propionate.

Workup

  1. additionThen, 1 g of activated carbon was added
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. washthe residue was subjected to silica gel column chromatography and elution

Sources & evidence

ORD record
ord-06ac218ebdef4ef4a5687c2521030d4e
Source dataset
uspto-grants-1998_11
Patent number
US05834460

Reaction notes

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