HCID 88506623, compound → HCID 131716371, compound

HRID 1650315Notes

Reaction equation

HRID 1650315 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH:12]([OH:59])[CH2:13][C:14](=O)[C@@H:15]([C@H:17]1[N:20]([C:21](=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C:19](=[O:47])[C@@H:18]1[C@H:48]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH3:49])[CH3:16])=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH:12]([OH:59])[CH2:13][C:14]1[C@H:15]([CH3:16])[C@H:17]2[N:20]([C:19](=[O:47])[C@@H:18]2[C@H:48]([O:50][Si:51]([C:54]([CH3:56])([CH3:55])[CH3:57])([CH3:53])[CH3:52])[CH3:49])[C:21]=1[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 88506623HCID 88506623, compound

Product 1

HCID 131716371HCID 131716371, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of allyl 2-[(3S,4R)-4-[(1R)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl)-4-hydroxy-1-methyl-2- oxobutyl]-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetate (2.36 g) in degassed toluene (120 ml) was heated to reflux for 8 hours. After cooling, the toluene was evaporated to give a residue of allyl (4S,5R,6S)-3-[2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl)-2-hydroxyethyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and the residue was taken up into dichloromethane (90.0 ml). To the mixture were added dropwise triethylamine (1.02 ml) and methane sulfonyl chloride (0.52 ml) at 5° C. with stirring and the stirring was continued for 30 minutes at 5° C. To the resultant mixture was added 1,8-diazabicyclo-[5.4.0]-7-undecene (3.36 ml) and the resultant mixture was allowed to warm to around 40° C. After stirring at 40° C. for 2 hours, the mixture was diluted with ethyl acetate and washed in turn with aqueous ammonium chloride, water and brine, and dried over magnesium sulfate. Removal of the solvent gave a residue, which was chromatographed on silica gel (150 ml) eluting with a mixture of n-hexane and ethyl acetate (9:1-4:1 V/V) to give allyl (4S,5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-ethenyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (1.12 g).

Workup

  1. temperatureto reflux for 8 hours
  2. temperatureAfter cooling
  3. customthe toluene was evaporated

Sources & evidence

ORD record
ord-965ad55d676e41aeaecb83cb8c21e080
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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