Ammonium formate → HCID 89647534, compound

HRID 2281008Notes

Reaction equation

HRID 2281008 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:22][NH:23]C(OCC2C=CC=CC=2)=O)([C:13](=[O:21])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.C(Cl)Cl.[Pd]>[NH2:23][CH2:22][C:10]1([C:13](=[O:21])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 89647803HCID 89647803, compound

Product 1

HCID 89647534HCID 89647534, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To 3-(benzyloxycarbonylamino-methyl)-3-phenylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1200.00 mg; 2.65 mmol; 1.00 eq.) in 30 ml of methanol was added of ammonium formate (1668.40 mg; 26.46 mmol; 10.00 eq.) and 10% Pd/C (wet) 1.2 g. The mixture was stirred at 65° C. for 1 hr and then filtered. The filtrate was concentrated to give the crude, which was dissolved in DCM and washed with 5% NaHCO3, brine, dried and concentrated to afford the title compound (820 mg, 97%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customto give the crude, which
  4. washwashed with 5% NaHCO3, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7fe3319b3b049de81d172e88d99620b
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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