Sulfuric Acid → HCID 59854684, compound

HRID 2112780Notes

Reaction equation

HRID 2112780 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([OH:26])[C:8]=2[S:9][C:10]=1[NH:11]C(=O)C)=[O:5])[CH3:2].OS(O)(=O)=O>CO>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([OH:26])[C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59854635HCID 59854635, compound2×

Product 1

HCID 59854684HCID 59854684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 01-6 (2.1 g, 5.7 mmol) was dissolved in MeOH (250 mL), H2SO4 (1 mL) was added and the mixture was stirred for 3 days. Another batch of 01-6 (450 mg, 1.2 mmol) was added and the mixture was stirred further for 14 days while monitoring the reaction each third day by HPLC. After completion the mixture was concentrated to half of the original volume. Water was added and the pH was cautiously adjusted to 8 with conc. NH4OH. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL) and dried over Na2SO4. The solvent was removed in vacuo to give product a-1 (2.05 g, 6.3 mmol, 91%) as a greenish brown foam.

Workup

  1. stirringthe mixture was stirred further for 14 days
  2. customthe reaction each third day by HPLC
  3. concentrationAfter completion the mixture was concentrated to half of the original volume
  4. additionWater was added
  5. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  6. washThe combined organic layers were washed with H2O (100 mL), brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo
  9. customto give product a-1 (2.05 g, 6.3 mmol, 91%) as a greenish brown foam

Sources & evidence

ORD record
ord-816ecaa653e9411193c267699960f1f4
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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