HCID 68673613, compound → HCID 68673858, compound

HRID 491176Notes

Reaction equation

HRID 491176 reaction equation
C([O:8][C:9]1[C:40]([CH3:41])=[CH:39][C:12]([CH2:13][C@@H:14]([CH2:18][C:19](=[O:38])[N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:22][CH2:21]2)[C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[O:42][CH3:43])C1C=CC=CC=1.[H][H]>C(N(CC)CC)C.CO.[Pd]>[OH:8][C:9]1[C:40]([CH3:41])=[CH:39][C:12]([CH2:13][C@@H:14]([CH2:18][C:19](=[O:38])[N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:24][CH2:25]2)[C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[O:42][CH3:43]

Participants

6

Reactant 2

HCID 68673613HCID 68673613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68673858HCID 68673858, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 7.60 g (12.98 mmol) (S)-2-(4-benzyloxy-3-methoxy-5-methyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid and 0.76 g 10% Pd/C in 2 mL triethylamine and 150 mL MeOH was hydrogenated at RT and 2620 hPa hydrogen pressure for 16 h. To complete the reaction a further 0.38 g 10% Pd/C were added and the mixture was again hydrogenated for 3 h at RT. The catalyst was filtered off through Celite and the filtrate was concentrated by evaporation i.vac. The product was further reacted without purification.

Workup

  1. customwas hydrogenated at RT
  2. additionwere added
  3. filtrationThe catalyst was filtered off through Celite
  4. concentrationthe filtrate was concentrated by evaporation i.vac
  5. customThe product was further reacted without purification

Sources & evidence

ORD record
ord-b01d832b2ef949fb81da83ac3584d02e
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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