Trifluoroacetic acid → HCID 137225434, compound

HRID 2292366Notes

Reaction equation

HRID 2292366 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]([CH:24]=[N:25][NH:26][S:27]([NH:30][C:31]([N:33]2[CH2:36][C@H:35]([NH:37]C(=O)OCC3C=CC=CC=3)[C:34]2=[O:48])=[O:32])(=[O:29])=[O:28])[CH:20]=[CH:21][C:22]=1[OH:23]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:37][C@H:35]1[CH2:36][N:33]([C:31]([NH:30][S:27]([NH:26][N:25]=[CH:24][C:19]2[CH:20]=[CH:21][C:22]([OH:23])=[C:17]([OH:16])[CH:18]=2)(=[O:28])=[O:29])=[O:32])[C:34]1=[O:48]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 136342840HCID 136342840, compound

Product 1

HCID 137225434HCID 137225434, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 22 ml of trifluoroacetic acid and 5.8 ml of thioanisole was cooled to 0° C., and 5.5 g (11.5 mmol) of (S)-[1-[[[[2-[(3,4-dihydroxyphenyl)methylene]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester were added. After stirring overnight at room temperature, the excess trifluoroacetic acid was evaporated in vacuo and the residue triturated with ether. The trifluoroacetic acid salt was filtered off by suction and dried in vacuo; yield: 2.64 g.

Workup

  1. customthe excess trifluoroacetic acid was evaporated in vacuo
  2. customthe residue triturated with ether
  3. filtrationThe trifluoroacetic acid salt was filtered off by suction
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4347d54c445743ed844faf99b9babdfb
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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