ethyl 1'-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4'-bipiperidinyl-4-carboxylate → ethyl 1'-[(R)-3-(4-hydroxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl]-1,4'-bipiperidinyl-4-carboxylate

HRID 599774Notes

Reaction equation

HRID 599774 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([O:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([N:46]3[CH2:52][CH2:51][C:50]4[CH:53]=[CH:54][CH:55]=[CH:56][C:49]=4[NH:48][C:47]3=[O:57])[CH2:42][CH2:41]2)=[O:39])[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[O:19])=[CH:11][C:10]=1[CH3:58])C1C=CC=CC=1.[H][H]>CCO.[Pd]>[OH:8][C:9]1[C:10]([CH3:58])=[CH:11][C:12]([CH2:16][C@@H:17]([O:37][C:38]([N:40]2[CH2:41][CH2:42][CH:43]([N:46]3[CH2:52][CH2:51][C:50]4[CH:53]=[CH:54][CH:55]=[CH:56][C:49]=4[NH:48][C:47]3=[O:57])[CH2:44][CH2:45]2)=[O:39])[C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]3)[CH2:24][CH2:25]2)=[O:19])=[CH:13][C:14]=1[CH3:15]

Participants

5

Reactant 2

HCID 67273670ethyl 1'-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4'-bipiperidinyl-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57832502ethyl 1'-[(R)-3-(4-hydroxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl]-1,4'-bipiperidinyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

80 mg (0.10 mmol) ethyl 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4′-bipiperidinyl-4-carboxylate in 10 mL EtOH were combined with 30 mg 10% Pd/C and hydrogenated at 50° C. and 50 psi hydrogen for 1 h. The catalyst was removed by suction filtering and the solvent was concentrated by evaporation i. vac. The residue was triturated with diethyl ether, suction filtered and dried.

Workup

  1. customThe catalyst was removed by suction
  2. filtrationfiltering
  3. concentrationthe solvent was concentrated by evaporation i
  4. customThe residue was triturated with diethyl ether, suction
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a6e2918ebb8a4dbea8c2f0d0093065db
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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