HCID 68611422, compound → HCID 11607118, compound

HRID 642839Notes

Reaction equation

HRID 642839 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH2:12][C@@H:13]([O:38][C:39]([N:41]2[CH2:46][CH2:45][CH:44]([N:47]3[CH2:53][CH2:52][C:51]4[CH:54]=[CH:55][CH:56]=[CH:57][C:50]=4[NH:49][C:48]3=[O:58])[CH2:43][CH2:42]2)=[O:40])[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:27][CH2:26][N:25](C(OCC4C=CC=CC=4)=O)[CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])[CH:3]=1.[H][H]>CO.[Pd]>[O:58]=[C:48]1[N:47]([CH:44]2[CH2:45][CH2:46][N:41]([C:39]([O:38][C@H:13]([CH2:12][C:4]3[CH:3]=[C:2]([CH3:1])[C:7]4[O:8][CH2:9][CH2:10][O:11][C:6]=4[CH:5]=3)[C:14](=[O:15])[N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)[CH2:18][CH2:17]3)=[O:40])[CH2:42][CH2:43]2)[CH2:53][CH2:52][C:51]2[CH:54]=[CH:55][CH:56]=[CH:57][C:50]=2[NH:49]1

Participants

5

Reactant 2

HCID 68611422HCID 68611422, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11607118HCID 11607118, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

35 mg (0.04 mmol) benzyl 4-(1-{(R)-3-(8-methyl-2,3-dihydro-1,4-benzodioxin-6-yl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-piperidin-4-yl)-piperazin-1-carboxylate (Example 6.12) were dissolved in 10 mL MeOH and combined with 50 mg 10% Pd/C. The mixture was hydrogenated at 50° C. and 3 bar hydrogen pressure until the theoretical hydrogen uptake had occurred (for 3 h). Then the catalyst was filtered off, the filtrate was evaporated to dryness i.vac., the residue was taken up in 2 mL DMF and purified by HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. customwas hydrogenated at 50° C.
  2. custom(for 3 h)
  3. filtrationThen the catalyst was filtered off
  4. customthe filtrate was evaporated to dryness i.vac
  5. custompurified by HPLC
  6. additionThe fractions containing the product

Sources & evidence

ORD record
ord-a88a5b9368ce4c6c8a1bbbccc6508ba6
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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