Methanol → (R)-2-(3,4-diamino-5-methyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 643097Notes

Reaction equation

HRID 643097 reaction equation
O=C1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18](OC)[C:19](=C=O)[C:20]3[CH:25]=[C:24]([N+:26]([O-])=O)[C:23]([NH2:29])=[C:22]([CH3:30])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1.[H][H].[CH3:41][OH:42]>>[O:42]=[C:41]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][C:20]3[CH:21]=[C:22]([CH3:30])[C:23]([NH2:29])=[C:24]([NH2:26])[CH:25]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 86601628(R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-methoxy-carbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68676807(R)-2-(3,4-diamino-5-methyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Procedure

A solution of 2.00 g (3.24 mmol) (R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-methoxy-carbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 3e, purity 85%) in 100 mL MeOH was hydrogenated for 3.5 h at 50° C. and 3447 hPa hydrogen pressure. The catalyst was filtered off and the filtrate was evaporated down i.vac. The residue was purified by chromatography (Alox, activity stage II-III, gradient DCM/MeOH 30:1 to 15:1).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac
  3. customThe residue was purified by chromatography (Alox, activity stage II-III, gradient DCM/MeOH 30:1 to 15:1)

Sources & evidence

ORD record
ord-923fc69ccaf341e6a3ff536eb2929167
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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