HCID 54440666, compound → HCID 44461096, compound

HRID 1069452Notes

Reaction equation

HRID 1069452 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:45])[C@@H:30]([NH:35][C:36]([N:38]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:37])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:25][CH2:24]2)[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:23]2[CH2:28][CH2:27][N:26]([C:29]([C@@H:30]([NH:35][C:36]([N:38]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:37])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:45])[CH2:25][CH2:24]2)=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 54440666HCID 54440666, compound

Product 1

HCID 44461096HCID 44461096, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[(S)-{4-[(1-{2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoyl}-piperidin-4-yl)-(3-methyl-butyl)-amino]-phenyl}-carbamic acid benzyl ester] (Example 34, 2.75 g, 4.34 mmol) was dissolved in THF/MeOH (50 mL, 1:1), treated with 20% Pd/C (0.26 g), and shaken under H2 (49 psi) for 1.25 hours. The reaction was filtered through Celite and concentrated to give 2.01 g (93%) of the desired product.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-36f22833966b4cbda5f5f5e76865b558
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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