Water → 3-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)-2,2-difluoropropanoic acid

HRID 1672137ノート

反応式

HRID 1672137 の反応式
[F:1][C:2]([F:8])([CH2:6][NH2:7])[C:3]([OH:5])=[O:4].[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[O:13]=[C:12]1[C:11]2[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:14])[N:7]1[CH2:6][C:2]([F:8])([F:1])[C:3]([OH:5])=[O:4]

参加物

6

反応物 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 27564053-Amino-2,2-difluoropropanoic acid

生成物 1

HCID 591583333-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)-2,2-difluoropropanoic acid収率 95.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 2,2-difluoro-3-aminopropionic acid A1 (7.08 g, 56.6 mmol) in 250 ml of toluene was treated with phthalic anhydride (8.80 g, 59.4 mmol) and triethylamine (20 mL, 14.35 g, 14.4 mmol) and refluxed with water removed by a Dean-Stark trap, drained 5 times at intervals. After cooling to ambient temperature the solvent was removed in vacuo at 30° C. The residue obtained was partitioned between ethyl acetate and ˜2N HCl (aq) with the aqueous phase extracted a second time with ethyl acetate. Evaporation at 30° C. (in vacuo) of the combined organic phases that had been washed with ˜2N HCl, brine and dried (Na2SO4) afforded 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2,2-difluoro-propionic acid (13.74 g) A2.

後処理

  1. customremoved by a Dean-Stark trap
  2. customwas removed in vacuo at 30° C
  3. customThe residue obtained
  4. customwas partitioned between ethyl acetate and ˜2N HCl (aq) with the aqueous phase
  5. extractionextracted a second time with ethyl acetate
  6. customEvaporation at 30° C. (in vacuo) of the combined organic phases that
  7. washhad been washed with ˜2N HCl, brine
  8. dry with materialdried (Na2SO4)

出典と根拠

ORDレコード
ord-babdaef1b7e34c8ca458a79625be3f03
出典データセット
uspto-grants-2011_08
特許番号
US07998950B2

反応ノート

読み込み中…