Sulfuric Acid → HCID 86696910, compound

HRID 1399999Notes

Reaction equation

HRID 1399999 reaction equation
[CH:1]12[O:7][C:6]1([C:8]1[N:13]=[CH:12][C:11]([C:14]3[CH:15]=[C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[C:17]4[S:21][C:20]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[N:19][C:18]=4[CH:28]=3)=[CH:10][N:9]=1)[CH2:5][CH2:4][O:3][CH2:2]2.S(=O)(=O)(O)[OH:36].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.O>[OH:7][CH:1]1[C:6]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:15]=[C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[C:17]4[S:21][C:20]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[N:19][C:18]=4[CH:28]=3)=[CH:10][N:9]=2)([OH:36])[CH2:5][CH2:4][O:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 86696909HCID 86696909, compound

Product 1

HCID 86696910HCID 86696910, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Compound iii (20 mg; 0.042 mmol) was dissolved in THF-H2O (10:1, 11 mL). Conc. sulfuric acid (20 μL) and p-toluenesulphonic acid (0.7 mg, 4 mmol) were added and the mixture stirred at RT. The mixture was concentrated in vacuo and purified over silica (0-100% 0.1% FA (aq)-MeCN) yielding Compound 8 (8.8 mg, 42%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified over silica (0-100% 0.1% FA (aq)-MeCN)

Sources & evidence

ORD record
ord-d75dc4592146492dbe2df547dc096648
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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