Diethyl Ether → HCID 131715842, compound

HRID 2292357Notes

Reaction equation

HRID 2292357 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:35])[CH2:11][NH:12][S:13]([NH:16][C:17]([N:19]2[CH2:22][C@H:21]([NH:23]C(=O)OCC3C=CC=CC=3)[C:20]2=[O:34])=[O:18])(=[O:15])=[O:14])[CH:5]=[CH:6][C:7]=1[OH:8].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].CCOCC>C1(SC)C=CC=CC=1>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[NH2:23][C@H:21]1[CH2:22][N:19]([C:17]([NH:16][S:13]([NH:12][CH2:11][C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=2)=[O:35])(=[O:15])=[O:14])=[O:18])[C:20]1=[O:34]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 86742710HCID 86742710, compound

Product 1

HCID 131715842HCID 131715842, compound

Reagents, catalysts & solvents 1

HCID 7520ThioanisoleSolvent

Procedure

To a suspension of 1.4 g (2.76 mmol) of (S)-[1[[[[[2-[(3,4-dihydroxyphenyl)amino]-2-oxoethyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester in 1.1 g of thioanisole was added 3 ml of trifluoroacetic acid and the mixture was stirred overnight at room temperature. 50 ml of ether was added and the resulting crystals were filtered off, washed twice with ether and finally triturated with dichloromethane; yield: 1.22 g.

Workup

  1. filtrationthe resulting crystals were filtered off
  2. washwashed twice with ether
  3. customfinally triturated with dichloromethane

Sources & evidence

ORD record
ord-d1fb79d8a91246eaacce46607bc9f90a
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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