4-Methylmorpholine → Methyl 2-amino-3-(2-(tert-butoxycarbonyl(methyl)amino)acetamido)benzoate

HRID 1517380Notes

Reaction equation

HRID 1517380 reaction equation
CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:32]([N:39]([CH2:41][C:42]([OH:44])=O)[CH3:40])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[NH2:45][C:46]1[C:55]([NH2:56])=[CH:54][CH:53]=[CH:52][C:47]=1[C:48]([O:50][CH3:51])=[O:49]>CN(C=O)C.O>[NH2:45][C:46]1[C:55]([NH:56][C:42](=[O:44])[CH2:41][N:39]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH3:40])=[CH:54][CH:53]=[CH:52][C:47]=1[C:48]([O:50][CH3:51])=[O:49]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 5718252,3-Diaminobenzoic acid methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58101623Methyl 2-amino-3-(2-(tert-butoxycarbonyl(methyl)amino)acetamido)benzoateYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

First N-methyl-morpholine (4 eq.) and then HATU (2.0 eq.) was added to a solution of N-Boc-sarcosine (30.12 mmol, 1.0 eq.) in DMF (3 ml/mmol) at 0° C. The reaction mixture was stirred at room temperature for 15 min and then cooled again to 0° C. in order to add a solution of methyl 2,3-diaminobenzoate (30.12 mmol, 1.0 eq.) in DMF (1 ml/mmol). The reaction mixture was then stirred at room temperature for 16 h. For working up, the reaction mixture was diluted with water and extracted with ethyl acetate and the organic phase was washed with sat. NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over Na2SO4 and concentrated in vacuo in order to obtain the crude product. This was purified by a column chromatography (silica gel) to obtain the desired product. Yield: 60%

Workup

  1. temperaturecooled again to 0° C. in order
  2. stirringThe reaction mixture was then stirred at room temperature for 16 h
  3. extractionextracted with ethyl acetate
  4. washthe organic phase was washed with sat. NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo in order
  7. customto obtain the crude product
  8. customThis was purified by a column chromatography (silica gel)

Sources & evidence

ORD record
ord-58fbccc5d7204e6ea14794cc890974bb
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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