4-Methylmorpholine → HCID 19705563, compound

HRID 727570Notes

Reaction equation

HRID 727570 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH:14]([C:18]2([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]2=[O:31])[C:15]([OH:17])=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CN1CCOCC1.Cl.[CH2:56]([O:63][NH2:64])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C(Cl)Cl>[CH2:56]([O:63][NH:64][C:15](=[O:17])[CH:14]([CH2:13][NH:12][S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:11])=[O:10])[C:18]1([CH2:32][CH:33]([CH3:34])[CH3:35])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 19705446HCID 19705446, compound

Product 1

HCID 19705563HCID 19705563, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of α-[[[(4-methoxyphenyl)sulfonyl]amino]methyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (290 mg, 0.577 mmol) in dry CH2Cl2 (5 mL) is treated with CDI (112 mg, 0.692 mmol). Afar 1 h, 4-methylmorpholine (0.095 mL, 0.866 mmol) and O-benzylhydroxyamine HCl (138 mg, 0.866 mmol) are added. The solution is stirred at room temperature under N2 for 65 h. The solvent had evaporated, and the residual gel is diluted with EtOAc (25 mL). The solution is washed with 1N HCl (10 mL), 1N NaOH (10 mL), and brine (10 mL). The organic layer is dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 380 mg of an oil. The oil is purified by silica gel chromatography (30 g SG; 50% EtOAc/hexane) to provide 249 mg (71%) of the title compound as an oil:

Workup

  1. customThe solvent had evaporated
  2. additionthe residual gel is diluted with EtOAc (25 mL)
  3. washThe solution is washed with 1N HCl (10 mL), 1N NaOH (10 mL), and brine (10 mL)
  4. dry with materialThe organic layer is dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da6ea128228042ba96f6c07953ed8696
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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