Toluene → HCID 57016436, compound

HRID 1090550Notes

Reaction equation

HRID 1090550 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[CH2:9][C@H:8]1[CH:18]=[C:19]([CH3:46])[C:20](=O)[CH2:21][C@H:22]1[N:25]([C:26](=O)[C:27]([O:29]CC=C)=O)[C:24](=[O:34])[C@@H:23]1[C@H:35]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH3:36])=[O:6])[CH:2]=[CH2:3].P([O:54][CH2:55][CH3:56])(OCC)OCC.[C:57]1(C)C=CC=CC=1>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][C:13](=[O:17])[N:14]([CH3:15])[CH3:16])[CH2:9][C@H:8]1[CH:18]=[C:19]([C:20]1[CH2:21][C@H:22]2[N:25]([C:24](=[O:34])[C@@H:23]2[C@H:35]([O:37][Si:38]([C:41]([CH3:43])([CH3:42])[CH3:44])([CH3:40])[CH3:39])[CH3:36])[C:26]=1[C:27]([O:54][CH2:55][CH:56]=[CH2:57])=[O:29])[CH3:46])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 31215Triethyl phosphiteHCID 67790986HCID 67790986, compound

Product 1

HCID 57016436HCID 57016436, compound

Conditions

Temperature
90 °C

Procedure

To a solution of allyl 2-[(3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]glyoxylate (0.44 g) in toluene (15 ml) was added triethyl phosphite (0.61 ml) and the resulting mixture was heated to 90° C. for 15 hours under nitrogen atmosphere. After evaporation of the solvent in vacuo, to the residue were added xylene (20 ml) and hydroquinone (20 mg) and the resulting mixture was heated to reflux for 10 hours under nitrogen atmosphere. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (50 ml) eluting with a mixture of n-hexane and ethyl acetate (8:2-1:1 V/V) to give allyl (5R,6S)-3-[2-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]- 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.26 g).

Workup

  1. customAfter evaporation of the solvent in vacuo
  2. additionto the residue were added xylene (20 ml) and hydroquinone (20 mg)
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 10 hours under nitrogen atmosphere
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel (50 ml)
  8. washeluting with a mixture of n-hexane and ethyl acetate (8:2-1:1 V/V)

Sources & evidence

ORD record
ord-fd10766af5de4aa1b98e83a4620f0392
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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