4-Methylmorpholine → HCID 54068794, compound

HRID 1590815Notes

Reaction equation

HRID 1590815 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[C:36]=1[C:37]([OH:39])=[O:38]>CN(C)C=O.O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([NH:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[C:36]=1[C:37]([OH:39])=[O:38])=[O:18])[CH:13]([CH3:14])[CH3:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 1512106-Methylanthranilic acidHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

Product 1

HCID 54068794HCID 54068794, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

After a tetrahydrofuran solution (40 ml) of N-benzyloxycarbonyl-D-valine (5.08 g) was cooled to -15° C., N-methylmorpholine (2.23 ml) and isobutyl chloroformate (2.61 ml) were added to the solution, and the mixture was stirred for 0.5 hour. An N,N-dimethylformamide solution (25 ml) containing 2-amino-6-methylbenzoic acid (2.04 g) and N-methylmorpholine (1.79 ml) was added dropwise to the above reaction mixture, and the resultant mixture was stirred at -15° C. for 0.5 hour and then at room temperature for two hours. The reaction mixture was treated by the same procedures as in item (c) of Example 1 to obtain 2-(N-benzyloxycarbonyl-D-valyl)amino-6-methylbenzoic acid (1.71 g).

Workup

  1. additionwas added dropwise to the above reaction mixture
  2. waitat room temperature for two hours

Sources & evidence

ORD record
ord-77ff04267b394c2284913bbbc906b0dc
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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