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

HRID 1354550ノート

反応式

HRID 1354550 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:22])([O:20][CH3:21])[NH2:19].CC(C)([O-])C.[Li+].O1CCCC1.O>O1CCCC1.C1(C)C=CC=CC=1>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([NH:19][C:18](=[O:22])[O:20][CH3:21])=[O:17])=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 11722Methyl CarbamateHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 86594548HCID 86594548、化合物

生成物 1

HCID 9944830methyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate収率 79%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

866 mg (3.57 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6 and 402 mg (5.4 mmol) of methyl carbamate were dissolved in tetrahydrofuran (15 mL) and further mixed with a lithium tert-butoxide/tetrahydrofuran solution (1 mol/L, 5.4 mL, 5.4 mmol) at room temperature. After stirring at the same temperature for 2 hours, water (5.0 mL) was further added to the reaction solution and extraction with toluene (10 mL) was repeated twice. The residue obtained by concentration of the separated organic layer after washing with water was purified on silica gel column chromatography to obtain methyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate as a white solid (897 mg, isolated yield: 79%). 1H-NMR (CDCl3, 400 MHz/ppm): 5 0.98 (3H, t), 1.5-1.8 (2H, m), 2.9-3.2 (2H, m), 3.77 (3H, s), 3.8-3.9 (1H, m), 4.2-4.3 (1H, br), 6.60 (2H, d), 7.37 (2H, d), 7.9-8.1 (1H, br)

後処理

  1. customThe residue obtained by concentration of the separated organic layer
  2. washafter washing with water
  3. customwas purified on silica gel column chromatography
  4. customto obtain

出典と根拠

ORDレコード
ord-829735fb5cb74cd3b76dd9744bef2051
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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