HCID 68673613, compound → HCID 68673858, compound

HRID 643165Notes

Reaction equation

HRID 643165 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-d809daf0ae7c4fbf9d2c8975f62345a2
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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