Sodium hydride → 2-{Thiophen-2-ylmethyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}acetic acid tert-butyl ester

HRID 1162584Notes

Reaction equation

HRID 1162584 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].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[H-].[Na+]>C1COCC1>[C:27]([O:26][C:24](=[O:25])[CH2:23][N:15]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:12]1[S:13][CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[N:11]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 24730368HCID 24730368, compound

Product 1

HCID 686478282-{Thiophen-2-ylmethyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}acetic acid tert-butyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution of [4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amine (80 mg, 0.25 mmol) and tert-butyl bromoacetate (41 μL, 0.28 mmol) was added NaH (15 mg, 60%, 0.38 mmol) and the resulting mixture was stirred at room temperature for 30 min. The reaction was quenched with brine and extracted with ethyl acetate (3×5 mL). Combined ethyl acetate extracts were dried over sodium sulfate, concentrated and purified on silica gel column to afford 2-{thiophen-2-ylmethyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}acetic acid tert-butyl ester (75 mg). LCMS m/z: 430 (M+1)+.

Workup

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. dry with materialCombined ethyl acetate extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified on silica gel column

Sources & evidence

ORD record
ord-e0f2ee5f8b284ff1b4186c352a7d5858
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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