Chloroform → HCID 86758353, compound

HRID 2229295Notes

Reaction equation

HRID 2229295 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[CH:10][NH:11][O:12][CH2:13][CH2:14][C@H:15]([NH:22]C(OCC1C=CC=CC=1)=O)[C:16]([N:18]([O:20][CH3:21])[CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl>CO.[Pd]>[NH2:22][C@@H:15]([CH2:14][CH2:13][O:12][NH:11][CH:10]=[N:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:16]([N:18]([O:20][CH3:21])[CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 86758354HCID 86758354, compound

Product 1

HCID 86758353HCID 86758353, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of (2S)-4-({[(tert-butoxy)carbonylamino]iminomethyl}aminooxy)-N-methoxy-N-methyl-2-[(phenylmethoxy)carbonylamino] butanamide (120 mg, 0.27 mmol), as prepared in the preceding step, and 10% Pd/C (18 mg) in methanol (5.0 mL) and chloroform (158 mL, 1.32 mmol) was hydrogenated with a balloon until all starting amine was consumed (in about 6 to 7 h). The mixture was filtered through Celite. The filtrate was concentrated to give the title compound (80 mg, 95% yield) as a colorless oil. Mass spectrum (LCMS, ESI) calcd. for C12H26N5O5 320.4 (M+H); found: 320.0.

Workup

  1. customwas consumed (in about 6 to 7 h)
  2. filtrationThe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1800a21a4edb4767880966baa0074d9a
Source dataset
uspto-grants-2002_07
Patent number
US06420397B1

Reaction notes

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