Triethylamine → HCID 67301221, compound

HRID 643626Notes

Reaction equation

HRID 643626 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:34]([OH:36])=[O:35])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26]CC4C=CC=CC=4)=[CH:22][CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:37]=[CH:38][CH:39]=[CH:40][C:4]=2[NH:3]1.C(N(CC)CC)C>CO.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:34]([OH:36])=[O:35])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:37]=[CH:38][CH:39]=[CH:40][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67301570HCID 67301570, compound

Product 1

HCID 67301221HCID 67301221, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

220 mg 10% Pd/C were added to a solution of 2.2 g (4.1 mmol) of (R)-1-carboxy-2-(4-benzyloxy-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate and 450 mg (4.4 mmol) triethylamine in 90 mL MeOH and the reaction mixture was hydrogenated at 3 bar H2 for 24 h. The catalyst was filtered, washed twice with MeOH and the filtrate was evaporated down i.vac. The residue was taken up in 20 mL water and adjusted to pH 2-3 with 10% HCl. The precipitate formed was filtered, washed with a little water and dried at 50° C.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed twice with MeOH
  3. customthe filtrate was evaporated down i.vac
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwashed with a little water
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-4a4cb0c8c8964cd2bfd6e4a6935ba0b8
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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