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Hydrochloric Acid → (S)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-propionic acid

HRID 76802
Notes
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Reaction equation

HRID 76802 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][C:28]2=[O:33])[C:22]=1[CH2:34][CH3:35])(=[O:20])=[O:19])[CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[O:8][N:7]=1.[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:16][C:13]1[S:12][C:11]([C:9]2[O:8][N:7]=[C:6]([CH2:5][C@H:4]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][C:28]4=[O:33])[C:22]=3[CH2:34][CH3:35])(=[O:20])=[O:19])[C:3]([OH:36])=[O:2])[CH:10]=2)=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66911103(S)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-propionic acid methyl ester

Product 1

HCID 66911167(S)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-propionic acid

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 7 (1.5 g, 2.71 mmol) in THF (15 ml), MeOH (5 ml) and water (5 ml) was treated with LiOH (194 mg, 8.12 mmol) and stirred at RT overnight. The mixture was acidified with HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried with MgSO4, filtered and evaporated to dryness. The crude product (1.3 g) was used without further purification in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product (1.3 g) was used without further purification in the next step

Sources & evidence

ORD record
ord-bbeba29e22a04a3a98f40a2768309dc9
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835653B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes