Hydrochloric Acid → HCID 68647842, compound

HRID 1162582Notes

Reaction equation

HRID 1162582 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+:23].[OH-:24].[Na+].Cl.[CH3:27][OH:28]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH2:2][CH2:1][CH2:4][CH2:5][C:27]([O-:28])=[O:24])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[Na+:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 24730368HCID 24730368, compound

Product 1

HCID 68647842HCID 68647842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To the THF solution of [4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amine (150.0 mg, 0.5 mmol) and methyl 5-bromopentaoate (215 μL, 0.1.5 mmol) was added NaH (60 mg, 60%, 0.1.5 mmol) and the resulting mixture was heated at 60° C. for 5 h, after cooling to room temperature methanol (2.0 ml). NaOH (2.0 ml, 1.0 M) added and mix was stirred at room temperature for 15 h. HCl added dropwise to pH 7.0. The acid was extracted with EtOAc (2×20 ml), combined organic extracts dried (Na2SO4), filtered, concentrated, and purified on silica gel column. The sodium salt was made following procedure J to afford the sodium 5-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-pentanoate (110 mg). LCMS m/z: 416 (M+1)+.

Workup

  1. additionmix
  2. extractionThe acid was extracted with EtOAc (2×20 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel column

Sources & evidence

ORD record
ord-e5b120a1e9714cc59d3099688d96a3d9
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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