Trifluoroacetic acid → HCID 131715849, compound

HRID 2292372Notes

Reaction equation

HRID 2292372 reaction equation
C1(SC)C=CC=CC=1.[OH:9][C:10]1[CH:11]=[C:12]([NH:17][S:18]([NH:21][C:22]([N:24]2[CH2:27][C@H:26]([NH:28]C(=O)OCC3C=CC=CC=3)[C:25]2=[O:39])=[O:23])(=[O:20])=[O:19])[CH:13]=[CH:14][C:15]=1[OH:16].[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[NH2:28][C@H:26]1[CH2:27][N:24]([C:22]([NH:21][S:18]([NH:17][C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([OH:9])[CH:11]=2)(=[O:20])=[O:19])=[O:23])[C:25]1=[O:39]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 131715850HCID 131715850, compound

Product 1

HCID 131715849HCID 131715849, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 10 ml of thioanisole and 40 ml of trifluoroacetic acid was cooled to 0° C., and 8.36 g (20 mmol) of (S)-[1-[[[[(3,4-dihydroxyphenyl)amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was added. The reaction mixture was stirred overnight at room temperature and the trifluoroacetic acid evaporated in vacuo. The oily residue was triturated with ether and the precipitate filtered off by suction. The crude product was washed with ether, dichloromethane and isopropanol and dried in vacuo; yield: 6.86 g.

Workup

  1. customthe trifluoroacetic acid evaporated in vacuo
  2. customThe oily residue was triturated with ether
  3. filtrationthe precipitate filtered off by suction
  4. washThe crude product was washed with ether, dichloromethane and isopropanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-97c40858bef240d88e31c53db385748b
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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