Diethyl Ether → HCID 14621660, compound

HRID 653863Notes

Reaction equation

HRID 653863 reaction equation
C([NH:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:54]/[O:55][CH2:56][F:57])/[C:27]([NH:29][C@@H:30]2[C:52](=[O:53])[N:32]3[C:33]([C:49]([O-:51])=[O:50])=[C:34](/[CH:37]=[CH:38]/[CH2:39][N+:40]([C@@H:43]([C:46](=[O:48])[NH2:47])[CH2:44][OH:45])([CH3:42])[CH3:41])[CH2:35][S:36][C@H:31]23)=[O:28])[N:22]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)C>C1(OC)C=CC=CC=1>[NH2:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:54]/[O:55][CH2:56][F:57])/[C:27]([NH:29][C@@H:30]2[C:52](=[O:53])[N:32]3[C:33]([C:49]([O-:51])=[O:50])=[C:34](/[CH:37]=[CH:38]/[CH2:39][N+:40]([C@@H:43]([C:46](=[O:48])[NH2:47])[CH2:44][OH:45])([CH3:42])[CH3:41])[CH2:35][S:36][C@H:31]23)=[O:28])[N:22]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acid2×HCID 141567064HCID 141567064, compound

Product 1

HCID 14621660HCID 14621660, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

The compound (500 mg) of Example 38 was suspended in anisole (3 ml), followed by an addition of trifluoroacetic acid (3.5 ml) under ice cooling. The resulting mixture was stirred for 1 hour at the same temperature, followed by a further addition of trifluoroacetic acid (1.5 ml). The resulting mixture was stirred for 1 hour. Ethyl ether was added, and a precipitate thus formed was collected by filtration to obtain the target product (350 mg). Its infrared spectrum and NMR spectrum were consistent with those of Example 10.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. customa precipitate thus formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3874ad21032e46c4963d1c557adc3f76
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

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