3-Fluorophenylacetic acid → HCID 67574108, compound

HRID 609648Notes

Reaction equation

HRID 609648 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH2:20][NH2:21])([CH3:15])([CH3:14])[CH3:13].Cl.C(N=C=N)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH2:20][NH:21][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 676173-Fluorophenylacetic acidHCID 187201N-BOC-ethylenediamineHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 67574108HCID 67574108, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluorophenylacetic acid (1.93 g, 12.5 mmol) in CH2Cl2 (50 mL) was added tert-butyl-N-(2-aminoethyl)carbamate (2.0 g, 12.5 mmol), 4-dimethylaminopyridine (1.53 g, 12.5 mmol) and 1-[3-dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (2.4 g, 12.5 mmol). The mixture was stirred at room temperature for 16 h then washed with water (50 mL) and citric acid (10%, 2×50 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (95:5→90:10), to afford the title amide (3.7 g, 100%) as a colourless solid. mp 125-128° C. 1H NMR (250 MHz, CDCl3) δ 1.43 (9H, s), 3.18-3.40 (4H, m), 3.53 (2H, s), 4.82 (1H, br s), 6.23 (1H, br s), 6.94-7.06 (3H, m), 7.26-7.40 (2H, m). MS (ES+) (297, M+1).

Workup

  1. washthen washed with water (50 mL) and citric acid (10%, 2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with CH2Cl2 :MeOH (95:5→90:10)

Sources & evidence

ORD record
ord-10cc67f427044e6d8287f455c2865572
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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