Water → benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate

HRID 1354551노트

반응식

HRID 1354551 반응식
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].[C:18](=[O:28])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:19].CC(C)([O-])C.[Li+].O1CCCC1.O>O1CCCC1.C(OCC)(=O)C>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:9]=[CH:8][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([NH:19][C:18](=[O:28])[O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:17])=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 12136Benzyl carbamateHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 86594548HCID 86594548, 화합물

생성물 1

HCID 10178731benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate수율 86%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

80.0 mg (0.33 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6and 74.8 mg (0.50 mmol) of benzyl carbamate were dissolved in tetrahydrofuran (3 mL) and further mixed with a lithium tert-butoxide/tetrahydrofuran solution (1 mol/L, 0.50 mL, 0.50 mmol) at room temperature. After stirring at the same temperature for 1.5 hours, water (5.0 mL) was further added to the reaction solution and extraction with ethyl acetate (5 mL) was repeated three times. The residue obtained by concentrating the separated organic layer dried with anhydrous magnesium sulfate was purified on silica gel column chromatography to obtain benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate as a white solid (112 mg, isolated yield: 86%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 0.98 (3H, t), 1.5-1.8 (2H, m), 2.9-3.2 (2H, m), 3.8-3.9 (1H, m), 4.2-4.3 (1H, br), 5.17 (2H, s), 6.60 (2H, d), 7.3-7.4 (7H, m), 7.5-7.6 (1H, br)

후처리

  1. customThe residue obtained
  2. concentrationby concentrating the separated organic layer
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customwas purified on silica gel column chromatography
  5. customto obtain

출처 및 근거

ORD 기록
ord-e9a091f3a70241b3b7484f1803ed2528
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223859B2

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