HCID 54149994, compound → HCID 15388997, compound

HRID 743994Notes

Reaction equation

HRID 743994 reaction equation
[CH2:1]([C:5]1[N:6]([CH3:29])[C:7]([C:10](=S)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C[O:31][C:32](=[O:46])[C:33](=[N+]=[N-])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]2[O:41][CH2:42][O:43][C:37]=2[CH:36]=1>CCOCC>[CH2:1]([C:5]1[N:6]([CH3:29])[C:7](/[C:10](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH2:20][C:21]([OH:23])=[O:22])=[C:33](\[CH2:34][C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][O:43][C:37]=3[CH:36]=2)/[C:32]([OH:46])=[O:31])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 54149994HCID 54149994, compoundHCID 54482180HCID 54482180, compound

Product 1

HCID 15388997HCID 15388997, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The freshly prepared 2-n-butyl-1-methyl-5-(2-t-butoxycarbonylmethoxy-4-methoxythiobenzoyl)-1H-imidazole (206 mg, 0.49 mmol) was dissolved in ether (2 ml) and methyl-2-diazo-3-(3,4-methylenedioxyphenyl)propionate as prepared in Example 1(g) (117 mg, 0.50 mmol) was added under argon. After standing at ambient temperature for 1 week, several drops of hexanes were added to the Et2O solution and the resulting white ppt (162 mg) was collected by filtration to afford the (2RS,3RS) isomer of the title compound. Further addition of hexanes and cooling afforded the (2RS,3SR) isomer as a pale pink solid (60 mg). The filtrate containing the title mixture of thiiranes was chromatographed on silica gel to afford complete separation. (167 mg, (2RS,3RS) isomer; 116 mg (2RS,3SR) isomer; 92%).

Workup

  1. additionwas added under argon
  2. waitAfter standing at ambient temperature for 1 week
  3. filtrationthe resulting white ppt (162 mg) was collected by filtration

Sources & evidence

ORD record
ord-bdca153887064022b21af95072ac8ab0
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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