2-Bromophenylacetic acid → HCID 22170862, compound

HRID 1822887Notes

Reaction equation

HRID 1822887 reaction equation
C1(N=C=N)CCCCC1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]([OH:20])=O.[NH2:21][C:22]1[S:23][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:25][N:26]=1>C(Cl)Cl>[CH:27]([C:24]1[S:23][C:22]([NH:21][C:18](=[O:20])[CH2:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Br:10])=[N:26][CH:25]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 877542-Bromophenylacetic acidHCID 104869545-(Propan-2-yl)-1,3-thiazol-2-amineHCID 12048208N-Cyclohexylcarbodiimide

Product 1

HCID 22170862HCID 22170862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of resin N-Cyclohexylcarbodiimide N′-methylpolystyrene (0.251 g, 2.39 mmol g, 0.6 mmol), previously washed with DCM (3×5 ml), in DCM (4 ml) at room temperature, 2-bromophenylacetic acid (0.086 g, 0.4 mmol) was added. After 10 min., a solution of 2-amino-5-isopropyl-1,3-thiazole (0.0284 g, 0.2 mmol) in DCM (4 ml) was added. The mixture was shaked for 24 hours at room temperature, the resin filtered and washed with DCM (3×10 ml). The filtrated were combined, washed with water, 5% HCl, water, saturated sodium bicarbonate and water, dried over sodium sulfate and evaporated.

Workup

  1. washpreviously washed with DCM (3×5 ml), in DCM (4 ml) at room temperature
  2. waitThe mixture was shaked for 24 hours at room temperature
  3. filtrationthe resin filtered
  4. washwashed with DCM (3×10 ml)
  5. washwashed with water, 5% HCl, water, saturated sodium bicarbonate and water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8c3ac90a0a7f43118f0278fee0729b89
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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