Dichloromethane methanol → HCID 66941742, compound

HRID 643128Notes

Reaction equation

HRID 643128 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 mmol) (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-28fdef73628743078f74c4a4e9ec6b15
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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