Trifluoromethanesulfonic acid → HCID 14659823, compound

HRID 484992Notes

Reaction equation

HRID 484992 reaction equation
[C:1]1([C:7]2[O:13][C@H:12]3[C@H:9]([C:10](=[O:34])[N:11]3[C:14]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:15]([CH3:17])[CH3:16])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+].[CH2:48]([O:50][C:51](=[O:55])[C@H:52]([CH3:54])[OH:53])[CH3:49]>>[CH2:48]([O:50][C:51]([C@H:52]([O:53][C@H:12]1[N:11]([C:14]([C:18]([O:20][CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:19])=[C:15]([CH3:16])[CH3:17])[C:10](=[O:34])[C@@H:9]1[NH:8][C:7](=[O:13])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:54])=[O:55])[CH3:49]

Participants

5

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 92831(L)-ethyl lactateHCID 516892Sodium BicarbonateHCID 13276947HCID 13276947, compound

Product 1

HCID 14659823HCID 14659823, compound

Procedure

10 Grams of (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-ene as used in Example 9(1) was dissolved in 35 ml of L-(+)-lactic acid ethyl ester instead of the DL-α-lactic acid ethyl ester employed in Reference Example 1(1). To the resultant solution was added 0.5 ml of trifluoromethanesulfonic acid, and the mixture was stirred at ambient temperature for 1.5 hours. The reaction solution thus obtained was poured into 200 ml of aqueous sodium bicarbonate and allowed to stand under ice-cooling for 30 minutes.

Workup

  1. customThe reaction solution thus obtained
  2. temperaturecooling for 30 minutes

Sources & evidence

ORD record
ord-75dcd903811b4511b2c3d86187fca76d
Source dataset
uspto-grants-1985_08
Patent number
US04534898

Reaction notes

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