Sulfuric Acid → HCID 70075384, compound

HRID 862429Notes

Reaction equation

HRID 862429 reaction equation
[ClH:1].[O:2]1[CH2:7][CH2:6][N:5]([N:8]=[CH:9][C:10]2[CH:32]=[CH:31][C:13]([C:14]([NH:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[O:23][CH2:22][CH:21]([CH2:27][C:28]([OH:30])=[O:29])[CH2:20]4)=[O:15])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.S(=O)(=O)(O)O>C(O)CCC>[ClH:1].[O:2]1[CH2:7][CH2:6][N:5]([N:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[O:23][CH2:22][CH:21]([CH2:27][C:28]([O:30][CH2:9][CH2:10][CH2:11][CH3:12])=[O:29])[CH2:20]4)=[O:15])=[CH:31][CH:32]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70076446HCID 70076446, compound

Product 1

HCID 70075384HCID 70075384, compoundYield 142.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

The compound (0.2 g) obtained in Example 5, was suspended in n-butanol. Concentrated sulfuric acid (0.1 ml) was dropwise added to the suspension and heated at 100° C. for an hour. The solvent was distilled off under reduced pressure and the concentrated residue was purified by reversed C18 column chromatography using a mixture, water:acetonitrile:trifluoroacetic acid=30:70:0.1, as a developer. The desired fraction was concentrated under reduced pressure. The concentrated residue was treated with a hydrochloric acid/dioxane solution to obtain the entitled compound (0.16 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe concentrated residue was purified by reversed C18 column chromatography
  3. concentrationThe desired fraction was concentrated under reduced pressure
  4. additionThe concentrated residue was treated with a hydrochloric acid/dioxane solution

Sources & evidence

ORD record
ord-0370a8009a3248adbba3112794b684e8
Source dataset
uspto-grants-1998_02
Patent number
US05719145

Reaction notes

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