Hydrochloric Acid → HCID 59136008, compound

HRID 1960514Notes

Reaction equation

HRID 1960514 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-c13227f670b44f1a9c85025b63b83101
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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