4-Methylmorpholine → HCID 53648128, compound

HRID 1590814Notes

Reaction equation

HRID 1590814 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:11][C:12](=[O:26])[C@H:13]([CH2:22][CH2:23][S:24][CH3:25])[NH:14][C:15]([O:17]C(C)(C)C)=O)[CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:42]([O:49][C:50]([N:52]1[CH2:59][CH2:58][CH2:57][C@H:53]1C(O)=O)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>Cl.O1CCOCC1.O1CCCC1.CN(C)C=O>[CH2:42]([O:49][C:50]([N:52]1[CH2:59][CH2:58][CH2:57][C@H:53]1[C:15]([NH:14][C@H:13]([C:12]([NH:11][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([OH:10])=[O:9])=[O:26])[CH2:22][CH2:23][S:24][CH3:25])=[O:17])=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-prolineHCID 54489752HCID 54489752, compound

Product 1

HCID 53648128HCID 53648128, compoundYield 37.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

6-methyl-2-[(N-tert-butoxycarbonyl-L-methionyl)amino]benzoic acid (346 mg) was dissolved in 4N-hydrochloric acid/dioxane (2.5 ml) stirred at room temperature for two hours. An N,N-dimethylformamide solution (2.5 ml) containing the residue obtained by concentrating and drying the above reaction solution and N-methylmorpholine (0.21 ml) was added to a tetrahydrofuran mixture, and the resultant solution was stirred at -15° C. for 0.5 hour. This tetrahydrofuran mixture was prepared by adding N-methylmorpholine (0.15 ml) and isobutyl chloroformate (0.17 ml) to a tetrahydrofuran solution (3.0 ml) of N-benzyloxycarbonyl-L-proline (328 mg) at -15° C. followed by stirring for 0.5 hour. The resultant reaction mixture was further stirred at room temperature for two hours and treated by the same procedures as in item (c) of Example 1 to obtain 2-(N-benzyloxycarbonyl-L-prolyl-L-methionyl)amino-6-methylbenzoic acid (173 mg).

Workup

  1. customobtained
  2. concentrationby concentrating
  3. dry with materialdrying the above reaction solution and N-methylmorpholine (0.21 ml)
  4. additionwas added to a tetrahydrofuran mixture
  5. stirringthe resultant solution was stirred at -15° C. for 0.5 hour
  6. customThis tetrahydrofuran mixture was prepared
  7. stirringby stirring for 0.5 hour
  8. customThe resultant reaction mixture
  9. stirringwas further stirred at room temperature for two hours

Sources & evidence

ORD record
ord-69a016b275154935ab4d2c9514b3e02d
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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