Water → HCID 53736911, compound

HRID 1283330Notes

Reaction equation

HRID 1283330 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[NH:23][C:22]2=[O:36])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:37]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])(=[O:40])[CH:38]=[O:39].O>C1C=CC=CC=1>[OH:39][CH:38]([N:23]1[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:21]([NH:20][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:22]1=[O:36])[C:37]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

Participants

5

Reactant 3

HCID 962WaterHCID 10986247Tert-butyl 2-oxoacetateHCID 53944058HCID 53944058, compound

Product 1

HCID 53736911HCID 53736911, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(Triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio)azetidin-2-one (1.02g) and t-butyl glyoxalate (2.76g) were refluxed in dry benzene (50ml) with provision for the removal of water. After 1 hour the benzene solution was washed 5 times with water, dried and evaporated. The residue was chromatographed on silica to give 1-(1-Hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (.969g).

Workup

  1. washAfter 1 hour the benzene solution was washed 5 times with water
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-a749e5abaa1941eca08fc15f153015ef
Source dataset
uspto-grants-1976_08
Patent number
US03974154

Reaction notes

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