Methanol → HCID 86744081, compound

HRID 2165272Notes

Reaction equation

HRID 2165272 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:15]([CH3:16])[N:14]([O:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])[C:13]1=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25]N(C1C=CC=CN=1)C.CO.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:15]([CH3:16])[N:14]([O:17][C:18]([CH3:23])([CH3:22])[C:19]([O:21][CH3:25])=[O:20])[C:13]1=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18640031HCID 18640031, compound

Product 1

HCID 86744081HCID 86744081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (3S-trans)-2-[[3-(benzyloxycarbonyl)amino4-methyl-2-oxo-1-azetidinyl]oxy]-2-methylpropanoic acid (1.68 g, 5.0 mmol) (see example 29) in 10 ml of dry dichloromethane were added 4 dimethylaminopyridine (30 mg), dry methanol 0.81 ml, 210 mmol) and dicyclohexylcarbodiimide (1.13 g, 5.5 mmol) at 0° C. The reaction mixture was stirred for 3 hours at room temperature. The precipitate (dicyclohexylurea) was removed by filtration and the filtrate was evaporated in vacuo. The residue was taken up in ether, filtered, washed with aqueous buffer solution pH 4 (citrate/HCl), NaHCO3 solution, dried over MgSO4 and filtered. Evaporation in vacuo gave the title compound.

Workup

  1. customThe precipitate (dicyclohexylurea) was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. filtrationfiltered
  4. washwashed with aqueous buffer solution pH 4 (citrate/HCl), NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation in vacuo

Sources & evidence

ORD record
ord-290429d4f2854dd1ab8cc666e0cb2b6e
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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