Tributylphosphine → (E)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

HRID 413934ノート

反応式

HRID 413934 の反応式
[CH3:1]/[C:2](/[C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH:3]\[CH2:4][OH:5].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:45]([O:47][C@@H:48]([CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][CH:56]=1)[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH3:46]>C1C=CC=CC=1>[CH2:52]([O:51][C:49](=[O:50])[C@@H:48]([O:47][CH2:45][CH3:46])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[C:6]#[C:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:57][CH:56]=1)[CH3:53]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 10797282(E)-3-methyl-5-phenyl-pent-2-en-4-yn-1-ol

生成物 1

HCID 10200538(E)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester収率 70.3%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

The title compound was prepared from of (E)-3-methyl-5-phenyl-pent-2-en-4-yn-1-ol (0.172 g, 1.0 mmol), (J. Med. Chem. 1998, 41(14), 2524-2536), tributylphosphine (0.370 mL, 1.5 mmol), 1,1′-(azodicarbonyl)dipiperidine (0.378 g, 1.5 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (0.262 g, 1.1 mmol) in dry benzene (20 mL) by a procedure analogous to that described in example 3, yielding 0.276 g (68%) of (E)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester. 1H NMR (300 MHz, CDCl3) δ: 1.1-1.25 (6H, m), 1.98 (3H, d), 2.95 (2H, d), 3.29-3.4 (1H, m), 3.53-3.65 (1H, m), 3.95 (1H, t), 4.15 (2H, q), 4.60 (2H, dd), 6.15 (1H, dt), 6.8 (2H, d), 7.15 (2H, d), 7.20-7.3 (3H, m), 7.35-7.45 (2H, m).

出典と根拠

ORDレコード
ord-b37fdb078e2346d7b05aa2df048830ea
出典データセット
uspto-grants-2003_05
特許番号
US06569901B2

反応ノート

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