Hydrochloric Acid → HCID 59136008, compound

HRID 504892Notes

Reaction equation

HRID 504892 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][N:6]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][C:21]([C:24]1[S:25][CH:26]([CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH2:27][N:28]=1)=[CH:20]2)[S:7]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)(=[O:9])=[O:8])C.[OH-].[K+].Cl>O1CCCC1.CO.O>[O:33]1[CH2:32][CH2:31][N:30]([CH2:29][CH:26]2[S:25][C:24]([C:21]3[NH:22][C:23]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][C:15]=4[N:6]([S:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)(=[O:8])=[O:9])[CH2:5][C:4]([OH:36])=[O:3])=[N:28][CH2:27]2)[CH2:35][CH2:34]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59135581HCID 59135581, compound

Product 1

HCID 59136008HCID 59136008, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-(2-thienylsulfonyl)glycine ethyl ester (120 mg) in tetrahydrofuran (3 mL) and methanol (3 mL) was added, under ice-cooling, a solution prepared by dissolving potassium hydroxide (purity 85%, 30 mg) in water (1 mL), and the mixture was stirred for 30 min, and then at room temperature for 1 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate-hexane to give the title compound (106 mg, yield 93%) as white crystals. MS: 521 (MH+).

Workup

  1. temperaturecooling
  2. customa solution prepared
  3. waitat room temperature for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record
ord-3cf2291f9ddd4d72bf4f0188b52c38b2
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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