Hydrochloric Acid → HCID 68648072, compound

HRID 1162592Notes

Reaction equation

HRID 1162592 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][N:7]([C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[N:19]=1)[CH2:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)C.[Li+].[OH-].[ClH:32]>[Cl-].[Na+].O>[ClH:32].[CH:26]([C:23]1[CH:22]=[CH:21][C:20]([C:18]2[N:19]=[C:15]([N:7]([CH2:8][CH2:9][C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH2:6][CH2:5][C:4]([OH:29])=[O:3])[S:16][CH:17]=2)=[CH:25][CH:24]=1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68648337HCID 68648337, compound

Product 1

HCID 68648072HCID 68648072, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To the 3-[[4-(4-isopropyl-phenyl)-thiazol-2-yl]-(2-thiophen-2-yl-ethyl)-amino]-propionic acid ethyl ester (95 mg, 0.22 mmol) was added LiOH (3 mL; 2N LiOH-MeOH-THF=1:1:4) and the reaction was stirred at room temperature for 4 h before acidifying with 1 N HCl. Brine was added, and the mixture was extracted with DCM (3×10 ml). The combined extracts were dried over Na2SO4, concentrated and purified on silica gel column to provide 3-[[4-(4-isopropyl-phenyl)-thiazol-2-yl]-(2-thiophen-2-yl-ethyl)-amino]-propionic acid hydrochloride salt (58 mg). LCMS m/z: 402 (M+1)+.

Workup

  1. extractionthe mixture was extracted with DCM (3×10 ml)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel column

Sources & evidence

ORD record
ord-f04169784f6845b5a21fcc6915495200
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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