Water → HCID 11724419, compound

HRID 966084Notes

Reaction equation

HRID 966084 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[CH:8]=[CH:7]C=1C(O)=O.[C:20]([N:27]1C=CN=C1)(N1C=CN=C1)=[O:21].C([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])C.[OH2:39]>C1COCC1>[C:20]([C@@H:37]([NH:34][C:35](=[O:39])[C:36]1[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:10][C:2]=1[F:1])[CH3:38])(=[O:21])[NH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22314484HCID 22314484, compound

Product 1

HCID 11724419HCID 11724419, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-fluoro-4-(3-fluoro-benzyloxy)-benzoic acid (400 mg, 1.5 mmol) and carbonyldiimidazole (258 mg, 1.6 mmol) in dry THF (5 mL) under Argon was heated under reflux for 30 min. After cooling to room temperature a suspension of H-alanine-NH2 HCl (226 mg, 1.8 mmol) containing triethylamine (184 mg, 1.8 mmol) in dry THF (1 mL) was added and the resulting mixture heated under reflux for 1 h. After cooling to room temperature water (5 mL) was added and the resulting precipitate was filtered off and washed successively with hexane and diethylether to afford the title compound (272 mg, 54%) as a white solid. MS: m/e=335.3 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. additiona suspension of H-alanine-NH2 HCl (226 mg, 1.8 mmol)
  4. additionwas added
  5. temperaturethe resulting mixture heated
  6. temperatureunder reflux for 1 h
  7. additionwas added
  8. filtrationthe resulting precipitate was filtered off
  9. washwashed successively with hexane and diethylether

Sources & evidence

ORD record
ord-284690db93af4cda9b24b14f64bbda47
Source dataset
uspto-grants-2005_10
Patent number
US06951884B2

Reaction notes

Loading…