HCID 59384418, compound → HCID 59384411, compound

HRID 2357071Notes

Reaction equation

HRID 2357071 reaction equation
C([O:8][C:9]1[CH:35]=[CH:34][C:12]([C:13]([NH:15][NH:16][C:17]([C@@:19]2([CH3:33])[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[N:20]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:18])=[O:14])=[CH:11][C:10]=1[C:36]([F:39])([F:38])[F:37])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:35]=[CH:34][C:12]([C:13]([NH:15][NH:16][C:17]([C@@:19]2([CH3:33])[CH2:23][O:22][C:21]([CH3:24])([CH3:25])[N:20]2[C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])=[O:18])=[O:14])=[CH:11][C:10]=1[C:36]([F:38])([F:39])[F:37]

Participants

4

Reactant 1

HCID 59384418HCID 59384418, compound

Product 1

HCID 59384411HCID 59384411, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl protected acyl-benzohydrazide 5b (1.0 equiv) in MeOH was subjected to hydrogenation in the presence of Pd/C (10% w) for 1 h. The reaction mixture was filtered through celite and concentrated to give compound 5c (6.86 g, 99% yield). MS (ESI, M+Na+): 484.0; TLC (2:1, Hex/EtOAc), Rf=0.20; 1H NMR (400 MHz, CD3OD) δ 8.11 (s, 1H,), 7.95 (d, 1H, J=8.8 Hz), 7.01 (d, 1H, J=8.8 Hz), 4.28 (br s, 1H), 3.91 (br s, 1H), 1.69 (s, 3H,), 1.64 (s, 3H), 1.58 (s, 3H), 1.49 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-750539f9ae704bfaa34d9e7287d5f72a
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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