Water → HCID 67151542, compound

HRID 1805230Notes

Reaction equation

HRID 1805230 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([C:25]3[C:26]4[CH:27]=[CH:28][N:29]=[CH:30][C:31]=4[CH:32]=[CH:33][CH:34]=3)(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.O.FC(F)(F)C(O)=O.[OH-].[Na+]>C(#N)C.C(OCC)(=O)C>[NH2:8][C@H:12]([CH2:11][OH:10])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([C:25]2[C:26]3[CH:27]=[CH:28][N:29]=[CH:30][C:31]=3[CH:32]=[CH:33][CH:34]=2)(=[O:24])=[O:23])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67151686HCID 67151686, compound

Product 1

HCID 67151542HCID 67151542, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(S)-4-{2-[4-(isoquinoline-5-sulfonylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (155 mg) was dissolved in acetonitrile (1.5 ml) and water (3 ml) before addition of trifluoroacetic acid (68.6 μl) at room temperature. The reaction mixture was then warmed to 50° C. and stirred for 5 hours and then cooled at room temperature and stirred for 12 hours. Ethyl acetate (4 ml) was added and then the solution basified by addition of 1N aqueous solution of sodium hydroxide until pH 14 followed by stirring for 15 minutes. The two layers were then separated and the aqueous was extracted twice with ethyl acetate, the combined organic layers were dried over Mg2SO4, filtered and concentrated in vacuo to give isoquinoline-5-sulfonic acid [4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-amide (109 mg) as a yellow solid. MS (ISP): 372.2 ([M+H]+).

Workup

  1. temperaturecooled at room temperature
  2. stirringstirred for 12 hours
  3. stirringby stirring for 15 minutes
  4. customThe two layers were then separated
  5. extractionthe aqueous was extracted twice with ethyl acetate
  6. dry with materialthe combined organic layers were dried over Mg2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51e306ec03f74fd9ba89cd0c2a010667
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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