Water → Succinic Acid

HRID 1576959Notes

Reaction equation

HRID 1576959 reaction equation
[CH3:1]/[CH:2]=[C:3]1\[C:4]2[S:8][CH2:7][CH:6]([C:9]([NH:11][CH:12]([C:108]([OH:113])([CH:110]([OH:112])[CH3:111])[CH3:109])[C:13]3[S:17][CH:16]=[C:15]([C:18]([NH:20][CH:21]4[C:60]5=[N:61][C:57](=[CH:58][S:59]5)[CH:56]5[N:62]=[C:63]([C:65]6[S:69][CH:68]=[C:67]([C:70]([NH:72][C:73]([C:75]([NH:77][C:78]([C:80]([NH2:82])=[O:81])=[CH2:79])=[O:76])=[CH2:74])=[O:71])[N:66]=6)[CH2:64][C:54]([C:83]6[S:87][CH:86]=[C:85]([C:88]([NH:90][CH:91]([CH:95]([OH:97])[CH3:96])[C:92]([NH:94]\1)=[O:93])=[O:89])[N:84]=6)([CH2:55]5)[NH:53][C:51](=[O:52])[CH:50]([CH3:98])[NH:49][C:47](=[O:48])[C:45](=[CH2:46])[NH:44][C:42](=[O:43])[C:40](=[CH2:41])[NH:39][C:37](=[O:38])[CH:36]([CH:99]([CH3:101])[CH3:100])[NH:35][CH:32]1[CH:33]([OH:34])[C:28]5=[C:29]([C:102]([CH:104]([OH:106])[CH3:105])=[CH:103][C:26](=[N:27]5)[C:24](=[O:25])[O:23][CH:22]4[CH3:107])[CH:30]=[CH:31]1)=[O:19])[N:14]=3)=[O:10])[N:5]=2.[C:114]1(=[O:120])[O:119][C:117](=[O:118])[CH2:116][CH2:115]1.[OH2:121].C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:1]/[CH:2]=[C:3]1\[C:4]2[S:8][CH2:7][CH:6]([C:9]([NH:11][CH:12]([C:108]([OH:113])([CH:110]([OH:112])[CH3:111])[CH3:109])[C:13]3[S:17][CH:16]=[C:15]([C:18]([NH:20][CH:21]4[C:60]5=[N:61][C:57](=[CH:58][S:59]5)[CH:56]5[N:62]=[C:63]([C:65]6[S:69][CH:68]=[C:67]([C:70]([NH:72][C:73]([C:75]([NH:77][C:78]([C:80]([NH2:82])=[O:81])=[CH2:79])=[O:76])=[CH2:74])=[O:71])[N:66]=6)[CH2:64][C:54]([C:83]6[S:87][CH:86]=[C:85]([C:88]([NH:90][CH:91]([CH:95]([OH:97])[CH3:96])[C:92]([NH:94]\1)=[O:93])=[O:89])[N:84]=6)([CH2:55]5)[NH:53][C:51](=[O:52])[CH:50]([CH3:98])[NH:49][C:47](=[O:48])[C:45](=[CH2:46])[NH:44][C:42](=[O:43])[C:40](=[CH2:41])[NH:39][C:37](=[O:38])[CH:36]([CH:99]([CH3:100])[CH3:101])[NH:35][CH:32]1[CH:33]([OH:34])[C:28]5=[C:29]([C:102]([CH:104]([OH:106])[CH3:105])=[CH:103][C:26](=[N:27]5)[C:24](=[O:25])[O:23][CH:22]4[CH3:107])[CH:30]=[CH:31]1)=[O:19])[N:14]=3)=[O:10])[N:5]=2.[C:117]([OH:119])(=[O:118])[CH2:116][CH2:115][C:114]([OH:120])=[O:121]

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 7922Succinic anhydrideHCID 1613027912656-09-6

Product 2

HCID 1110Succinic AcidHCID 1613027912656-09-6

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Siomycin A (10.0 g) is dissolved in pyridine (60 ml) and butanedioic acid anhydride (6.0 g) is added to the mixture. The resultant mixture is kept with stirring at 93° to 95°C for an hour in oil bath. Distilled water (60 ml) and chloroform (100 ml) are added to the reaction mixture, and then the resultant solution is vigorously shaken. The chloroform phase is evaporated under reduced pressure to remove the solvent, then benzene is added to the resulting residue. The benzene-insoluble part is dissolved in a mixture of chloroform and methanol (8 : 2 by volume). The resulting mixture is chromatographed on a column of silica gel (particle size 0.05-0.2 mm, made by Merk company) and eluted with a mixture of chloroform and methanol with a progressively increasing concentration of methanol. The fractions containing the half ester of siomycin A with butanedioic acid are collected and concentrated. The concentrated solution is applied to a silica gel GF plate (made by Merk company) and the plate is developed with a mixture of chloroform and methanol (8 : 2 by volume). The part containing the half ester -I of siomycin A with butanedioic acid is extracted with a mixture of chloroform and methanol and the resulting solution is concentrated. To the concentrated solution is added ethyl acetate to obtain the half ester of siomycin A with butanedioic acid (precipitate). The yield is 60%.

Workup

  1. customThe chloroform phase is evaporated under reduced pressure
  2. customto remove the solvent
  3. additionbenzene is added to the resulting residue
  4. dissolutionThe benzene-insoluble part is dissolved in a mixture of chloroform and methanol (8 : 2 by volume)
  5. customThe resulting mixture is chromatographed on a column of silica gel (particle size 0.05-0.2 mm, made by Merk company)
  6. washeluted with a mixture of chloroform and methanol with
  7. temperaturea progressively increasing concentration of methanol
  8. additionThe fractions containing the half ester of siomycin A with butanedioic acid
  9. customare collected
  10. concentrationconcentrated
  11. additionthe plate is developed with a mixture of chloroform and methanol (8 : 2 by volume)
  12. additionThe part containing the half ester
  13. extractionof siomycin A with butanedioic acid is extracted with a mixture of chloroform and methanol
  14. concentrationthe resulting solution is concentrated
  15. additionTo the concentrated solution is added ethyl acetate

Sources & evidence

ORD record
ord-e6e1ee30e8dc4b549947d0897ba8e509
Source dataset
uspto-grants-1976_09
Patent number
US03983230

Reaction notes

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