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

HRID 1354550노트

반응식

HRID 1354550 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: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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-829735fb5cb74cd3b76dd9744bef2051
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223859B2

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