HCID 136360279, compound → HCID 136360278, compound

HRID 1157891Notes

Reaction equation

HRID 1157891 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6]([NH:8][C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 136360279HCID 136360279, compound

Product 1

HCID 136360278HCID 136360278, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

The alcohol (0.282 g, 0.771 mmol) from above was dissolved in CH2Cl2 (7 mL), treated with activated MnO2 (0.696 g, 8.01 mmol) and stirred at room temperature overnight. The mixture was filtered through Celite© and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced pressure and provided N,N′-bis-(tert-butoxycarbonyl)-N″-(4-formyl-phenyl)-guanidine (0.260 g, 93%) as a white solid. 1H NMR (CDCl3) δ 1.53 (s, 9H), 1.55 (s, 9H), 7.85 (s, 4H), 9.93 (s, 1H), 10.34 (br s, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite©
  2. washthe cake was washed with CH2Cl2
  3. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-fd151f2922e14714a882fececbe8f821
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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