Hydrochloric Acid → HCID 58392516、化合物

HRID 561517ノート

反応式

HRID 561517 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[N:18](C(OC(C)(C)C)=O)[CH:17]=2)[CH:9]([CH3:15])[C:10](OCC)=[O:11])=[C:4]([F:35])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:9]([CH3:15])[CH2:10][OH:11])=[C:4]([F:35])[CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392467HCID 58392467、化合物

生成物 1

HCID 58392516HCID 58392516、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 200 mg of the compound from Example 36A with a purity of 90% (0.35 mmol) in 4 ml of tetrahydrofuran was added dropwise to 1.2 ml (1.2 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 2 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 15 min and then 1N hydrochloric acid was added. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 66 mg (51% of theory) of the title compound as mixture of diastereomers.

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-415ff0bf62244d4597ae2b82417b2ad7
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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