Citric Acid → HCID 86747318, compound

HRID 1609055Notes

Reaction equation

HRID 1609055 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.[NH2:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:35]2[C:44]([F:45])=[CH:43][C:42]3[C:46](=[O:52])[C:47]([C:49]([OH:51])=[O:50])=[CH:48][N:40]4[C:41]=3[C:36]=2[CH2:37][CH2:38][N:39]4[CH3:53])[CH2:30]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:35]2[C:44]([F:45])=[CH:43][C:42]3[C:46](=[O:52])[C:47]([C:49]([OH:51])=[O:50])=[CH:48][N:40]4[C:41]=3[C:36]=2[CH2:37][CH2:38][N:39]4[CH3:53])[CH2:30]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9928823HCID 9928823, compound

Product 1

HCID 86747318HCID 86747318, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

350 mg (2 mmol) of N-t-butoxycarbonylglycine and 202 mg (2 mmol) of N-methylmorpholine were added to 6 ml of methylene chloride. The mixture solution was cooled on freezing mixture, and 0.26 ml (2 mmol) of isobutyl chlorocarbonate was added to the solution. After 20 minutes, 716 mg (2 mmol) of the compound (30) obtained in Example 5 (1) was added to the solution, and the solution was stirred at room temperature for 30 minutes. Then, 10 ml of water was added to the solution, and the solution was acidified with by citric acid. The organic layer was separated from the solution and was removed distillation after drying over sodium sulfate. Ethyl acetate-ether was added to the residue, then the product came out of the solution, and the solid was filtered off to obtain 776 mg of the subject compound (84) in a 75% yield. The results of the analysis of this compound were as follows:

Workup

  1. temperatureThe mixture solution was cooled
  2. additionwas added to the solution
  3. customThe organic layer was separated from the solution
  4. customwas removed
  5. distillationdistillation
  6. dry with materialafter drying over sodium sulfate
  7. additionEthyl acetate-ether was added to the residue
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-e2894ba99ea748be85fb05980812fa48
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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