Sodium Sulfate → HCID 57539220, 화합물

HRID 601959노트

반응식

HRID 601959 반응식
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:30][C:31]([F:39])(S(F)(=O)=O)C(O)=O>C(#N)C>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([CH2:14][O:15][CH:31]([F:39])[F:30])[C:10]([O:12][CH3:13])=[O:11])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 24436Sodium SulfateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 4184069Methyl 2-(dibenzylamino)-3-hydroxypropanoate

생성물 1

HCID 57539220HCID 57539220, 화합물수율 4.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To an acetonitrile solution of methyl 2-(dibenzylamino)-3-hydroxypropanoate (23 g, 76.8 mmol) and sodium sulfate (3.9 g, 27.4 mmol) at 40° C., difluoro(fluorosulfonyl)acetic acid (25 g, 140 mmol) was added dropwise for 1.5 hrs. The reaction mixture was concentrated to dryness and the residue mixed with silica gel in ethyl acetate, then again concentrated to dryness. The product was purified by column chromatography, eluting with 3-4% ethyl acetate in hexanes, to give methyl 2-dibenzylamino-3-difluoromethoxy-propionate (1.3 g, 4.8%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.20-7.40 (m, 10H), 6.18 (bt, 1H), 4.05-4.24 (m, 2H), 3.90 (d, 2H), 3.83 (s, 3H) and 3.64-3.71 (m, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionthe residue mixed with silica gel in ethyl acetate
  3. concentrationagain concentrated to dryness
  4. customThe product was purified by column chromatography
  5. washeluting with 3-4% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-dedddc9ad10d4f58b49bde7f166b4d89
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902401B2

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