4-Methylmorpholine → HCID 54489752, compound

HRID 1590813Notes

Reaction equation

HRID 1590813 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35]([OH:37])=[O:36]>CN(C)C=O.O1CCCC1>[CH3:42][C:38]1[C:34]([C:35]([OH:37])=[O:36])=[C:33]([NH:32][C:14](=[O:16])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 89857Boc-L-methionineHCID 1512106-Methylanthranilic acid

Product 1

HCID 54489752HCID 54489752, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

After a tetrahydrofuran solution (12.4 ml) of N-tert-butoxycarbonyl-L-methionine (1.24 g) was cooled to -15° C., N-methylmorpholine (0.55 ml) and isobutyl chloroformate (0.60 ml) were added to the solution, and the mixture was stirred for 20 minutes. Subsequently, an N,N-dimethylformamide solution (8.27 ml) containing 2-amino-6-methylbenzoic acid (0.50 g) and N-methylmorpholine (0.44 ml) was added dropwise, and the mixture was stirred at -15° C. for 0.5 hour and then at room temperature overnight. The reaction mixture was treated by the same procedures as in item (c) of Example 1 to obtain 6-methyl-2-[(N-tert-butoxycarbonyl-L-methionyl)amino]benzoic acid (348 mg).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at -15° C. for 0.5 hour
  3. customat room temperature
  4. customovernight

Sources & evidence

ORD record
ord-9c873c2668a347aebc2be0434018d463
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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