Acetic Acid → (3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

HRID 64803

反応式

HRID 64803 の反応式
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[I-].[K+].[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C:36](=[O:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(O)(=O)C>C(OCC)(=O)C.C(OCC)C>[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C@H:36]([OH:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 14127274(3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

生成物 1

HCID 13104625(3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one収率 84.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

K-Selectride ® (3.64 ml of 0.5M, 1.82 mmol) is added by syringe to a mixture of potassium iodide (126 mg., 0.758 mmol) and (3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one (298 mg, 0758 mmol) in freshly distilled ethyl ether (8 ml) at room temperature. The resulting mixture is stirred at room temperature for 2.5 hours, then quenched by the addition of acetic acid (218 mg., 3.64 mmol). The resulting mixture is diluted with ethyl acetate (25 ml) and filtered through celite. Removal of solvents in vacuo gives an oil which is chromatographed on silica gel (ether:petroleum ether) to yield 252 mg of (3S, 4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one. N.M.R. (R isomer, CDCl3 +D2O) δ4.15(dq,1), δ3.95(ddd,1,J=9.5,2.3), δ3.26(dd,1,J=8,2.3), δ 2.37(m,2), δ2.16(s,9), δ1.37(d,3,J=6,6), δ1.0(s,9), δ0.26(s,6).

後処理

  1. filtrationfiltered through celite
  2. customRemoval of solvents in vacuo
  3. customgives an oil which
  4. customis chromatographed on silica gel (ether:petroleum ether)

出典と根拠

ORDレコード
ord-8aba69f318e84134a651316dc6c1ce79
出典データセット
uspto-grants-1986_09
特許番号
US04610820

関連ノート

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