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-carboxylic acid → 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-carboxylic acid

HRID 599775Notes

Reaction equation

HRID 599775 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([O:35][C:36]([N:38]2[CH2:43][CH2:42][CH:41]([N:44]3[CH2:50][CH2:49][C:48]4[CH:51]=[CH:52][CH:53]=[CH:54][C:47]=4[NH:46][C:45]3=[O:55])[CH2:40][CH2:39]2)=[O:37])[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[O:19])=[CH:11][C:10]=1[CH3:56])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([O:35][C:36]([N:38]2[CH2:39][CH2:40][CH:41]([N:44]3[CH2:50][CH2:49][C:48]4[CH:51]=[CH:52][CH:53]=[CH:54][C:47]=4[NH:46][C:45]3=[O:55])[CH2:42][CH2:43]2)=[O:37])[C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]3)[CH2:24][CH2:25]2)=[O:19])=[CH:11][C:10]=1[CH3:56]

Participants

5

Reactant 2

HCID 672736911'-{(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-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 578325051'-{(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-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 mg (0.13 mmol) 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-carboxylic acid in 10 mL MeOH were combined with 30 mg 10% Pd/C and hydrogenated at 50° C. and 3 bar hydrogen for 2 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-70e40846386e4310988ea72a453e72ac
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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