Dichloromethane methanol → HCID 66941742, compound

HRID 491139Notes

Reaction equation

HRID 491139 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:36]([OH:38])=[O:37])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27]CC4C=CC=CC=4)=[C:22]([Cl:35])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1.[H][H].C(Cl)Cl.CO>C1COCC1>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:36]([OH:38])=[O:37])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[C:22]([Cl:35])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 21226129Dichloromethane methanolHCID 66941845HCID 66941845, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66941742HCID 66941742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg 5% Rh on aluminium oxide were added to a solution of 800 mg (1.35 m mol) (R)-2-(4-benzyloxy-3-chloro-5-methyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 20 mL THF and the suspension was hydrogenated for 12 h at 40° C. and 3000 hPa hydrogen pressure. To complete the reaction the mixture was combined with 5 mL DCM/MeOH (1:1) and hydrogenated for a further 20 h at 40° C. and 3000 hPa. The catalyst was filtered off, the filtrate was evaporated down, the residue was triturated with DIPE, suction filtered and dried.

Workup

  1. customthe reaction the mixture
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated down
  4. customthe residue was triturated with DIPE, suction
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-6107acbbb1c541cc9463d9ef7772099c
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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