D-Lactic Acid → HCID 178462369、化合物

HRID 40852

反応式

HRID 40852 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH2:4][CH2:3]1.[C:18](O)(=[O:22])[C@@H:19]([CH3:21])[OH:20].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[OH:20][C@H:19]([CH3:21])[C:18]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH2:4][CH2:3]1)=[O:22]

参加物

6

反応物 4

HCID 61503D-Lactic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178462199HCID 178462199、化合物

生成物 1

HCID 178462369HCID 178462369、化合物収率 41%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Trans-tert-butyl (R)-1-(4-aminocyclohexyl)ethylcarbamate (125 mg, 0.52 mmol) was dissolved in DMF (3 mL). D-Lactic Acid (49.52 mg, 0.52 mmol), diisopropylethylamine (166.6 mg, 224.5 μL, 1.29 mmol) and TBTU (165.6 mg, 0.5158 mmol) were successively added. The reaction mixture was allowed to stir at ambient temperature for 3 hours. The crude mixture was partitioned between ethyl acetate and brine. The organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM) to afford the title compound (66.1 mg, 41% yield).

後処理

  1. customThe crude mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-7f8733391c0a42b8b5a5e55392f268ff
出典データセット
uspto-grants-2013_09
特許番号
US08530489B2

関連ノート

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