Trimethylsilyldiazomethane → Methyl 3-Methyl-4-phenyl-2-(2,2,2-trifluoroacetamido)-(2S,3R)-pent-4-enoate

HRID 707724노트

반응식

HRID 707724 반응식
[CH3:1][C@H:2]([C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:15])[C@H:3]([NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[C:4]([OH:6])=[O:5].[CH3:22][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[CH3:1][C@H:2]([C:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH2:15])[C@H:3]([NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[C:4]([O:6][CH3:22])=[O:5]

참가 물질

4

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 533554023-Methyl-4-phenyl-2-(2,2,2-trifluoroacetamido)-(2S,3R)-pent-4-enoic Acid

생성물 1

HCID 53355012Methyl 3-Methyl-4-phenyl-2-(2,2,2-trifluoroacetamido)-(2S,3R)-pent-4-enoate수율 81%

시약·촉매·용매 1

HCID 21867641Toluene methanol용매

실험 절차

Carboxylic acid 14 (544.4 mg, 1.81 mmol) was placed in 1:1 CH3OH-toluene (6 mL) under N2, and trimethylsilyldiazomethane (2 M solution in hexane, 4.0 mL, 8.0 mmol) was added. The solution was stirred at ambient temperature for 16 h. The solvent was evaporated, and the residue was chromatographed (silica gel, 17 g; 9:1 hexane-EtOAc) to yield 0.46 g (81%) of 15 as a colorless oil: Rf0.54 (4:1 hexane-EtOAc); 1H NMR δ 7.33 (5H, m), 6.48 (1H, br d), 5.34 (1H, s), 5.11 (1H, d, J=0.8 Hz), 4.64 (1H, dd, J=8.7 and 4.0 Hz), 3.76 (3H, s), 3.48 (1H, m), 1.26 (3H, d, J=7.1 Hz).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed (silica gel, 17 g; 9:1 hexane-EtOAc)

출처 및 근거

ORD 기록
ord-94700439d2a64f4db98348d30699e570
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175041B2

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