Sodium hydride → HCID 68648337, compound

HRID 1162591Notes

Reaction equation

HRID 1162591 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].[H-].[Na+]>C1COCC1>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][CH2:30][N:15]([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)[CH2:16][CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 86079793HCID 86079793, compound

Product 1

HCID 68648337HCID 68648337, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution of [4-(4-isopropyl-phenyl)-thiazol-2-yl]-(2-thiophen-2-yl-ethyl)-amine (100 mg, 0.3 mmol) and ethyl bromopropionate (42 μL, 0.33 mmol) was added NaH (18 mg, 60%, 0.45 mmol). The mixture was stirred at room temperature for 30 min, and the excess NaH was quenched with brine and extracted into ethyl acetate (3×5 mL). The combined ethyl acetate extracts were dried over sodium sulfate, concentrated and purified on silica gel column to afford 3-[[4-(4-isopropyl-phenyl)-thiazol-2-yl]-(2-thiophen-2-yl-ethyl)-amino]-propionic acid ethyl ester (98 mg). LCMS m/z: 430 (M+1)+.

Workup

  1. customthe excess NaH was quenched with brine
  2. extractionextracted into ethyl acetate (3×5 mL)
  3. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified on silica gel column

Sources & evidence

ORD record
ord-f4c6b9ee5240452baa1d9f835d1a6434
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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