Ammonium formate → HCID 23373648, compound

HRID 865926Notes

Reaction equation

HRID 865926 reaction equation
[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]([N:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[C:5](=[O:24])[CH:4]([NH:25]C(=O)OCC2C=CC=CC=2)[N:3]=1.C([O-])=O.[NH4+]>[Pd].CO.O>[NH2:25][CH:4]1[N:3]=[C:2]([CH3:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]([N:16]([CH3:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:15])[C:5]1=[O:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53855886HCID 53855886, compound

Product 1

HCID 23373648HCID 23373648, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 5% palladium on carbon (300 mg) and phenylmethyl [2,3-dihydro-5-methyl-1-[2-(methylphenylamino)-2-oxoethyl]-2-oxo-1H-1,4-benzodiazepin-3-yl]carbamate (500 mg) in MeOH-water 4:1(40 ml) at 40° under nitrogen was treated with ammonium formate (201 mg) and the mixture stirred at 40° for 1 h. The mixture was cooled to 23° and was filtered through hyflo. The filtrate was evaporated in vacuo and the residue partitioned between 2 N sodium carbonate solution and chloroform. The organic phase was dried and the solvent evaporated in vacuo. The residue was purified by chromatography, elution with MeOH-DCM (1:9) gave the title compound(302 mg).

Workup

  1. temperatureThe mixture was cooled to 23°
  2. filtrationwas filtered through hyflo
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue partitioned between 2 N sodium carbonate solution and chloroform
  5. customThe organic phase was dried
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by chromatography, elution with MeOH-DCM (1:9)

Sources & evidence

ORD record
ord-b25771903dd5424db496fc735abe5c76
Source dataset
uspto-grants-1996_10
Patent number
US05569654

Reaction notes

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