Ammonium Chloride → HCID 58844429, compound

HRID 1271117Notes

Reaction equation

HRID 1271117 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH2:25][C:26](O)=[O:27])[CH:22]=[CH:23][CH:24]=1)=[O:18])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN.C1COCC1.Cl.[CH2:37]([N:39]=C=NCCCN(C)C)C.[Cl-].[NH4+]>ClCCl>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH2:25][C:26]([NH:39][CH3:37])=[O:27])[CH:22]=[CH:23][CH:24]=1)=[O:18])[CH3:10])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 58844200HCID 58844200, compoundHCID 66615946Methylamine tetrahydrofuran2×

Product 1

HCID 58844429HCID 58844429, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl]acetyl}phenyl)acetic acid (2.62 g) prepared in reference example 16, 4-dimethylaminopyridine (78 mg) and 2.0M methylamine/THF (3.3 ml) in dichloromethane (25 ml) was added at 0° C. 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (1.24 g) and the mixture was stirred for 6 hours. Further, 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (0.13 g) and 2.0M methylamine/THF (0.33 ml) were added thereto and the mixture was reacted overnight. To the mixture was added an aqueous saturated ammonium chloride solution (50 ml) and the mixture was extracted with ethyl acetate.(100 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (2×50 ml), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give 2-(3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl]acetyl}phenyl)-N-methylacetamide (1.96 g).

Workup

  1. additionwas added at 0° C
  2. customthe mixture was reacted overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution (2×50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-0cc35c364079473b939a18141c94bb26
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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