Trifluoroacetic acid → HCID 131715851, compound

HRID 2292375Notes

Reaction equation

HRID 2292375 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C1(SC)C=CC=CC=1.[OH:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:28][CH2:27][N:26]([S:29]([NH:32][C:33]([N:35]3[CH2:38][C@H:37]([NH:39]C(=O)OCC4C=CC=CC=4)[C:36]3=[O:50])=[O:34])(=[O:31])=[O:30])[C:25]2=[O:51])[CH:20]=[CH:21][C:22]=1[OH:23]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:39][C@H:37]1[CH2:38][N:35]([C:33]([NH:32][S:29]([N:26]2[CH2:27][CH2:28][N:24]([C:19]3[CH:20]=[CH:21][C:22]([OH:23])=[C:17]([OH:16])[CH:18]=3)[C:25]2=[O:51])(=[O:30])=[O:31])=[O:34])[C:36]1=[O:50]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 86742712HCID 86742712, compound

Product 1

HCID 131715851HCID 131715851, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 16 ml of trifluoroacetic acid and 4 ml of thioanisole was cooled to 0° C., and 4 g (7.7 mmol) of (S)-[1-[[[[3-(3,4-dihydroxyphenyl)-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was added. The mixture was stirred overnight at room temperature, evaporated in vacuo, and the residue triturated with ether. The precipitate was filtered off by suction, washed with ether, dichlormethane and isopropanol and dried in vacuo; yield: 3.19 g.

Workup

  1. customevaporated in vacuo
  2. customthe residue triturated with ether
  3. filtrationThe precipitate was filtered off by suction
  4. washwashed with ether, dichlormethane and isopropanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dfac3678b7634a5baed3d55b7a5ef353
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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