Potassium Carbonate → HCID 19424222, compound

HRID 743152Notes

Reaction equation

HRID 743152 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:48]=[CH:49][C:50]=1[C:51]([O:53]C)=[O:52])[CH2:5][NH:6][C:7](=[O:47])[CH:8]([S:19][S:20][CH:21]([CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:40][CH:39]=1)[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([O:34]C)=[O:33])=[C:28]([OH:36])[CH:27]=1)=[O:23])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:22](=[O:23])[CH:21]([S:20][S:19][CH:8]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[C:7]([NH:6][CH2:5][C:4]2[CH:48]=[CH:49][C:50]([C:51]([OH:53])=[O:52])=[C:2]([OH:1])[CH:3]=2)=[O:47])[CH2:37][C:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][CH:39]=2)=[CH:27][C:28]=1[OH:36])([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19424231HCID 19424231, compound

Product 1

HCID 19424222HCID 19424222, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Hydrolysis of 57 (0.28 g) with K2CO3 in MeOH/water at 50° C. for 5 hours, under nitrogen as above, gave an oil. Chromatography on silica gel, eluting with EtOAc:light petroleum (1:1) containing 1% AcOH, gave 2,2'-dithiobis[N-(4-carboxy-3-hydroxybenzyl)-3-(3-indolyl)propanamide] (58) [VI: n=2; R1 =R3 =H, R2 =(CH2)2CONHCH2Ph{3-OH, 4-COOH}] (72 mg, 27% mp (MeOH/dilute HCl) 160°-163.5° C. (dec).

Workup

  1. customunder nitrogen as above, gave an oil
  2. washChromatography on silica gel, eluting with EtOAc:light petroleum (1:1)
  3. additioncontaining 1% AcOH

Sources & evidence

ORD record
ord-d919d8e553aa484786ad54a424d025d4
Source dataset
uspto-grants-1996_09
Patent number
US05556874

Reaction notes

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