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Dimethylformamide → N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine

HRID 2923
Notes
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Reaction equation

HRID 2923 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.Cl.[CH3:46][O:47][C:48]1[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]([O:56][CH3:57])[C:49]=1[NH2:50]>C(OC(C)C)(C)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10](=[O:12])[NH:50][C:49]1[C:51]([O:56][CH3:57])=[CH:52][C:53]([CH3:55])=[CH:54][C:48]=1[O:47][CH3:46])=[O:2])([CH3:5])([CH3:6])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 189364892,6-Dimethoxy-4-methylaniline hydrochloride

Product 1

HCID 18936465N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamineYield 96%

Reagents, catalysts & solvents 3

HCID 7914Diisopropyl EtherSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at room temperature for 15 hours. 400 ml of ethyl acetate are added to the reaction mixture and the organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution and then with water. The organic phase is dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a semi-crystalline residue which is solidified in diisopropyl ether to provide N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine, in the form of white crystals; M.p.=146° C.; Yield: 96%.

Workup

  1. waitThe reaction mixture is left at room temperature for 15 hours
  2. washthe organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution
  3. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customleaves a semi-crystalline residue which

Sources & evidence

ORD record
ord-9cb77feee68640b1aefc6e6668171bff
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731340

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes