Hydrochloric Acid → HCID 13091039, compound

HRID 435399Notes

Reaction equation

HRID 435399 reaction equation
[NH:1]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:56][CH2:55][CH2:54][C@H:23]1[C:24]([NH:26][C@H:27]([C:37]([N:39]1[CH2:53][CH2:52][CH2:51][C@H:40]1[C:41]([O:43]CC1C=CC=CC=1)=[O:42])=[O:38])[CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:25])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO>[NH:1]([C:57]([O:59][C:60]([CH3:62])([CH3:61])[CH3:63])=[O:58])[C@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:56][CH2:55][CH2:54][C@H:23]1[C:24]([NH:26][C@H:27]([C:37]([N:39]1[CH2:53][CH2:52][CH2:51][C@H:40]1[C:41]([OH:43])=[O:42])=[O:38])[CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:25])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13091037HCID 13091037, compound

Product 1

HCID 13091039HCID 13091039, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The substance [20] (74.4 g, 85.4 mM) was dissolved in methanol (300 ml), and 1 N NaOH (110 ml, 1.3 molar excess) was added dropwise at 0° C., and the mixture was stirred at room temperature for three hours. After neutralizing at 0° C. by adding 1 N HCl (26 ml), the methanol was distilled off in vacuo. The aqueous layer was washed twice with ether, 1 N HCl (86 ml) was added at 0° C. and then was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried with anhydrous magnesium sulfate and concentrated in vacuo. Hexane was added to the residue and the thus-formed precipitate was filtered. The precipitate was dissolved in a small amount of chloroform and charged on a column of silica gel packed with chloroform. Elution was carried out with chloroform, chloroform-ethyl acetate (1:1) and chloroform-ethanol-ethyl acetate (5:1:5). The fractions corresponding to the substance as checked by TLC were collected and dried in vacuo to obtain the substance [21] (53.75 g, yield: 81%).

Workup

  1. customAfter neutralizing at 0° C.
  2. distillationthe methanol was distilled off in vacuo
  3. washThe aqueous layer was washed twice with ether, 1 N HCl (86 ml)
  4. additionwas added at 0° C.
  5. extractionwas extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed twice with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. additionHexane was added to the residue
  10. filtrationthe thus-formed precipitate was filtered
  11. dissolutionThe precipitate was dissolved in a small amount of chloroform
  12. additioncharged on a column of silica gel
  13. washElution
  14. customwere collected
  15. customdried in vacuo

Sources & evidence

ORD record
ord-a186d2b1f6594019b50f63bf39e0cafd
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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