Dimethylcarbamoylmethyl 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 → dimethylcarbamoylmethyl 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 599777Notes

Reaction equation

HRID 599777 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([O:41][C:42]([N:44]2[CH2:49][CH2:48][CH:47]([N:50]3[CH2:56][CH2:55][C:54]4[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=4[NH:52][C:51]3=[O:61])[CH2:46][CH2:45]2)=[O:43])[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][C:36](=[O:40])[N:37]([CH3:39])[CH3:38])=[O:33])[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[O:19])=[CH:11][C:10]=1[CH3:62])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[OH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([O:41][C:42]([N:44]2[CH2:49][CH2:48][CH:47]([N:50]3[CH2:56][CH2:55][C:54]4[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=4[NH:52][C:51]3=[O:61])[CH2:46][CH2:45]2)=[O:43])[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][C:36](=[O:40])[N:37]([CH3:39])[CH3:38])=[O:33])[CH2:28][CH2:27]3)[CH2:24][CH2:25]2)=[O:19])=[CH:11][C:10]=1[CH3:62]

Participants

5

Reactant 2

HCID 67273082Dimethylcarbamoylmethyl 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 57832548dimethylcarbamoylmethyl 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 8028TetrahydrofuranSolvent

Procedure

95 mg (0.11 mmol) dimethylcarbamoylmethyl 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 THF were combined with 50 mg 10% Pd/C and hydrogenated at 50° C. and 50 psi hydrogen for 6 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.vac
  4. customThe residue was triturated with diethyl ether, suction
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-7a50724246ab475abbe4085df2fea3d6
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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