Water → HCID 178488017, compound

HRID 1007307Notes

Reaction equation

HRID 1007307 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]1[NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[C:28]([NH:38]CC2C=CC(OC)=CC=2)[N:27]=1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1.O>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:14]([O:13][C:11]([NH:10][C:9]([NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]1[NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[C:28]([NH2:38])[N:27]=1)=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 178491030HCID 178491030, compound

Product 1

HCID 178488017HCID 178488017, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.76 g of (1R,2S)-N-[N,N′-bis(tert-butoxycarbonyl)]amidino-2-[2-(4-methoxybenzylamino)-6-methoxyquinazolin-4-yl]aminocyclohexylamine in 80 mL of methylene chloride was combined with 3.17 g of N-methylmorpholine-N-oxide and 95 mg of tetrapropylammonium perruthenate, and stirred for 9 hours. The reaction solution was combined with water, extracted with methylene chloride, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform:methanol 10:1) to obtain 0.95 g of the desirable compound.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by column chromatography on silica gel (chloroform:methanol 10:1)

Sources & evidence

ORD record
ord-58917d6fb03742d7a8c9279c9353593c
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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