4-Methylmorpholine → HCID 10296107, compound

HRID 642163Notes

Reaction equation

HRID 642163 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1)=[O:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[NH2:40]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:40][NH:39][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:19])=[CH:15][CH:14]=2)=[O:10])=[CH:22][CH:23]=1)=[O:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 70091tert-Butyl carbazateHCID 9879821HCID 9879821, compound

Product 1

HCID 10296107HCID 10296107, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution of 4-({[4-(methoxycarbonyl)benzoyl]amino}methyl)benzoic acid (1.0 g, 3.19 mmol) and N-methyl morpholine (420 μL, 3.83 mmol) in anhydrous THF (25 mL) at 0° C. was added isobutyl chloroformate (455 μL, 3.51 mmol) then tert-butyl hydrazine carboxylate (1.12 mg, 7.66 mmol). After stirring at 0° C. for 1 hr and overnight at rt, the reaction mixture was quenched with HCl (1N, 25 mL). Extraction with EtOAc (2×25 mL), drying over MgSO4 and evaporation under vacuo gave a residue. Purification by flash chromatography (SiO2, EtOAc) gave the title compound (773 mg, 55%) as a white powder.

Workup

  1. customthe reaction mixture was quenched with HCl (1N, 25 mL)
  2. extractionExtraction with EtOAc (2×25 mL)
  3. dry with materialdrying over MgSO4 and evaporation under vacuo
  4. customgave a residue
  5. customPurification by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-d3d8ac7860b3404986eb6db33fade405
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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