Isopropanol → HCID 69037641, compound

HRID 1820795Notes

Reaction equation

HRID 1820795 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:16].[CH3:18][CH:19](O)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CN=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH-].[Na+]>C1COCC1>[CH:13]1([S:10]([C:8]2[CH:7]=[CH:6][C:5]([O:16][CH:19]([CH3:20])[CH3:18])=[C:4]([CH:9]=2)[C:3]([OH:2])=[O:17])(=[O:12])=[O:11])[CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 97268Di-tert-butyl azodicarboxylateHCID 6218932-PyridyldiphenylphosphineHCID 69036806HCID 69036806, compound

Product 1

HCID 69037641HCID 69037641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.6 mmol 5-cyclopropanesulfonyl-2-hydroxy-benzoic acid methyl ester, 3.7 mmol 2-propanol and 0.9 mmol diphenyl-2-pyridylphosphine in 8 ml THF was added 0.9 mmol di-tert-butyl azodicarboxylate, and the mixture was stirred at RT for 3 h. 4 mmol 5 M aq NaOH solution was then added, and the mixture heated at 60° C. for 1 h. The mixture was then concentrated in vacuo. The residue was resuspended in ethyl acetate and washed twice with 1 M aq NaOH solution. The combined aqueous phases were then acidified to pH 1 by addition of 25% aq HCl and extracted three times with ethyl acetate. The combined organic extracts were then dried with Na2SO4, and concentrated in vacuo to afford the title compound. MS (m/e): 282.9 ([M−H]−, 100%)

Workup

  1. temperaturethe mixture heated at 60° C. for 1 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. washwashed twice with 1 M aq NaOH solution
  4. additionThe combined aqueous phases were then acidified to pH 1 by addition of 25% aq HCl
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts were then dried with Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be744b69ac9644018d29e64faeb119d4
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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