Water → HCID 21517661, compound

HRID 1283334Notes

Reaction equation

HRID 1283334 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[CH:24]([S:25][CH2:26][C:27]#[C:28][CH3:29])[NH:23][C:22]2=[O:30])([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:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[CH:32]=[O:33].O>C1C=CC=CC=1>[OH:33][CH:32]([N:23]1[CH:24]([S:25][CH2:26][C:27]#[C:28][CH3:29])[CH:21]([NH:20][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:22]1=[O:30])[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 10986247Tert-butyl 2-oxoacetateHCID 21517634HCID 21517634, compound

Product 1

HCID 21517661HCID 21517661, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(Triphenylmethylamino)-4-(but-2-ynylthio)azetidin-2-one (1.03g) and t-butyl glyoxalate (3.3 g) were refluxed in dry benzene (50ml) with provision for the removal of water. After one hour the benzene solution was washed 5 times with water, dried and evaporated. Chromatography of the residue on silica -H gave 1-(1-hydroxy-1-t-butoxycarbonylmethyl)-3-(triphenylmethylamino)-4-(but-2-ynylthio)azetidin-2-one as an amorphous white solid (0.978 g)

Workup

  1. washAfter one hour the benzene solution was washed 5 times with water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-e5ee1a19294b4957bf74e36d9d42a673
Source dataset
uspto-grants-1976_08
Patent number
US03974154

Reaction notes

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