1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 15223703, compound

HRID 1033454Notes

Reaction equation

HRID 1033454 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([OH:19])=O)[CH3:16])[N:13]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]1=[O:28])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[SH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(OCC)C.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([S:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:19])[CH3:16])[N:13]([CH2:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:12]1=[O:28])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10476973(3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-1-(t-butyloxycarbonylmethyl)azetidin-2-oneHCID 178418616HCID 178418616, compound

Product 1

HCID 15223703HCID 15223703, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-1-(t-butyloxycarbonylmethyl)azetidin-2-one (100 mg) and 2-mercaptopyridine (35 mg) in dry tetrahydrofuran (4 ml), there was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (100 mg) under ice-cooling, followed by stirring overnight. The reaction mixture was diluted with diethyl ether and water. The organic layer was separated from the aqueous layer, washed with brine, dried over sodium sulfate and distilled off to remove the solvent to give (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(2-pyridylthio)carbonylethyl]-1-(t-butyloxycarbonylmethyl)azetidin-2-one.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated from the aqueous layer
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled off
  6. customto remove the solvent

Sources & evidence

ORD record
ord-a405789b8de54e8789da346249caff9a
Source dataset
uspto-grants-1994_05
Patent number
US05310897

Reaction notes

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