Trifluoroacetic acid → HCID 131715834, compound

HRID 2292338Notes

Reaction equation

HRID 2292338 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:53]=[CH:54][C:55]=1[OH:56])[C:20]([NH:22][N:23]1[CH2:28][CH2:27][N:26]([S:29]([NH:32][C:33]([N:35]2[CH2:38][C@H:37]([NH:39]C(=O)OCC3C=CC=CC=3)[C:36]2=[O:50])=[O:34])(=[O:31])=[O:30])[C:25](=[O:51])[C:24]1=[O:52])=[O:21]>CCOCC>[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:23]([NH:22][C:20](=[O:21])[C:19]3[CH:53]=[CH:54][C:55]([OH:56])=[C:17]([OH:16])[CH:18]=3)[C:24](=[O:52])[C:25]2=[O:51])(=[O:30])=[O:31])=[O:34])[C:36]1=[O:50]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 131715835HCID 131715835, compound

Product 1

HCID 131715834HCID 131715834, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 12 ml of trifluoroacetic acid and 3 ml of thioanisole was added 2.92 g (4.94 mmol) of (S)-[1-[[[[4-[(3,4-dihydroxybenzoyl)amino]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester at 0° C. After stirring overnight at 10° C., 150 ml of ether was added and the resulting precipitate was filtered off, washed with ether and dried in vacuo. For further purification, the salt was triturated two times with dichloromethane; yield: 2.56 g; melting point 206°-210° C.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with ether
  3. customdried in vacuo
  4. customFor further purification
  5. customthe salt was triturated two times with dichloromethane

Sources & evidence

ORD record
ord-c81fbce4c1ad4fb0a01665a9d81f956e
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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