Phosgene → methyl (5R)-3-[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate

HRID 1991297

반응식

HRID 1991297 반응식
[O:1]=[S:2]1(=[O:24])[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([NH:15][CH2:16][C@@H:17]([OH:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:10][C:9]=2[F:23])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33]>C(Cl)Cl.C1(C)C=CC=CC=1>[O:24]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([C:8]2[C:9]([F:23])=[CH:10][C:11]([N:15]3[CH2:16][C@H:17]([C:18]([O:20][CH3:21])=[O:19])[O:22][C:32]3=[O:33])=[CH:12][C:13]=2[F:14])[CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 86610079methyl (2R)-3-{[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]amino}-2-hydroxypropanoate

생성물 1

HCID 68489310methyl (5R)-3-[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxylate수율 83%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of methyl (2R)-3-{[4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenyl]amino}-2-hydroxypropanoate (Step 1, 1.02 g, 2.90 mmol) in CH2Cl2 (25 mL) and triethylamine (1.0 g, 1.5 mL, 10.5 mmol) is cooled to 0° C. and treated with phosgene (1.94 mL of a 20% solution in toluene, 3.6 mmol). After stirring at room temperature for one hour, the reaction mixture is diluted with CH2Cl2 and washed with dilute NaHCO3, saline, and dried (MgSO4), filtered and concentrated. Chromatography on silica gel (10% acetonitrile-dichloromethane) provides the title compound (0.91 g, 83%), MS (m/z): [M+H]+=391; 1H NMR (300 MHz, CDCl3): δ 3.16-3.20 (m, 4H), 3.64 (m, 4H), 3.88 (s, 3H), 4.06-4.11 (m, 1H), 4.23 (t, 1H), 5.06-5.11 (m, 1H), 7.16 (d, 2H).

후처리

  1. washwashed with dilute NaHCO3, saline
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dbabb24ae365441da9c0a83e4646097c
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645781B2

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