Trifluoroacetic acid → (S)-3-Amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine

HRID 2292346Notes

Reaction equation

HRID 2292346 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][NH:13][S:14]([NH:17][C:18]([N:20]2[CH2:23][C@H:22]([NH:24]C(=O)OCC3C=CC=CC=3)[C:21]2=[O:35])=[O:19])(=[O:16])=[O:15])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1>CCOCC>[NH2:24][C@H:22]1[CH2:23][N:20]([C:18]([NH:17][S:14]([NH:13][NH:12][C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=2)=[O:11])(=[O:16])=[O:15])=[O:19])[C:21]1=[O:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 86742705(S)-[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Product 1

HCID 53662062(S)-3-Amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 0° C., 1.02 g (2.0 mmol) of (S)-[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was added to a mixture of 3.31 ml of trifluoroacetic acid and 0.78 ml (6.63 mmol) of thioanisole. After stirring overnight at room temperature, the dark brown solution was dropped into 40 ml of dry ether (0° C.) and the precipitated material was collected by suction (1.15 g) and stirred with 10 ml of dry dichloromethane; yield: 0.92 g. This material was used in the next step without further purification.

Workup

  1. customthe precipitated material was collected by suction (1.15 g)
  2. stirringstirred with 10 ml of dry dichloromethane
  3. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-49c7943a0d254af48eb4091ee2ec4eab
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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