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

HRID 1354551ノート

反応式

HRID 1354551 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-e9a091f3a70241b3b7484f1803ed2528
出典データセット
uspto-grants-2007_05
特許番号
US07223859B2

反応ノート

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