Triethylamine → methyl (2R)-2-{[tert-butyl(diphenyl)silyl]oxy}propanoate

HRID 445096

反応式

HRID 445096 の反応式
[CH3:1][O:2][C:3](=[O:7])[C@H:4]([OH:6])[CH3:5].C(N(CC)CC)C.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.CCOC(C)=O>[Si:15]([O:6][C@H:4]([CH3:5])[C:3]([O:2][CH3:1])=[O:7])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 637514(+)-Methyl lactate

生成物 1

HCID 58726730methyl (2R)-2-{[tert-butyl(diphenyl)silyl]oxy}propanoate収率 99.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To the mixture of (R)-2-Hydroxy-propionic acid methyl ester (1.0 g, 9.6 mmol), triethyl amine (4.0 mL, 28.81 mmol) in tetrahydrofuran (12 mL), was added tert-butyldiphenylsilylchloride (3.68 mL, 14.4 mmol) at room temperature and allowed the reaction mixture to stir for 12 h. After completion of the reaction, the reaction mixture was diluted with EtOAc (80 mL) and washed with water (70 mL) and brine (70 mL). The EtOAc layer was dried over Na2SO4 and solvent was evaporated in vacuo to afford methyl (2R)-2-{[tert-butyl(diphenyl)silyl]oxy}propanoate (3.28 g). The above crude material was sufficiently pure for the next step and used without further purification. The crude material was diluted with THF-MeOH—H2O (1:1:1, 20 mL) and added LiOH. H2O (1.17 g, 28.0 mmol). The reaction mixture was stirred for over night at room temperature. The reaction mixture neutralized with conc.HCl and concentrated in vacuo. The residue was diluted with 75 mL water and extracted with EtOAc (3×50 mL), the combined EtOAc layers were dried over Na2SO4 and evaporated in vacuo. The crude carboxylic acid was purified by Isco silica gel flash column using EtOAc to obtain the carboxylic acid (0.6 g). 1H NMR (CDCl3) δ 7.70-7.60 (m, 4H), 7.50-7.38 (m, 6H), 4.32 (q, J=6.6 Hz, 1H), 1.30 (d, J=7.0 Hz, 9H); LC-MS [M−H]+ 327.2

後処理

  1. customAfter completion of the reaction
  2. washwashed with water (70 mL) and brine (70 mL)
  3. dry with materialThe EtOAc layer was dried over Na2SO4 and solvent
  4. customwas evaporated in vacuo

出典と根拠

ORDレコード
ord-c8d917d0542a47078eb8b318b2ba6c1f
出典データセット
uspto-grants-2013_07
特許番号
US08476285B2

関連ノート

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