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

HRID 1672137노트

반응식

HRID 1672137 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-babdaef1b7e34c8ca458a79625be3f03
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998950B2

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