Hydrochloric Acid → methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(R)-fluoropropionate

HRID 1008286ノート

反応式

HRID 1008286 の反応式
[CH2:1]([C@@H:5]([C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([O:21]C(C)(C)C)=[O:20])=[O:13])[C@@H:6]([F:11])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH3:4].Cl>O1CCOCC1>[CH2:1]([C@@H:5]([C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([OH:21])=[O:20])=[O:13])[C@@H:6]([F:11])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 59908476methyl 3-(S)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)-2-(R)-fluoropropionate

生成物 1

HCID 59908545methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(R)-fluoropropionate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To methyl 3-(S)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)-2-(R)-fluoropropionate G-4 (2.3 mmol) was added 4 N HCl in dioxane (10 mL), the solution stirred for 2 h, then evaporated to dryness to afford 2.3 mmol of methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(R)-fluoropropionate G-5 (quant.). To intermediate G-5 (0.15 mmol) in dioxane (1 mL) was added an amine (0.15 mmol), DIEA (0.38 mmol), and HATU or other coupling reagent (0.15 mmol) and the solution stirred for 8 h. The reaction was cooled to 0° C., aqueous 50% hydroxylamine was added (0.5 mL) and the reaction stirred for 4 h. The crude reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford N-hydroxy-3-(S)-n-butyl-3-[2-(S)-aminocarbonylpyrrolidin-1-ylcarbonyl)-2-(R)-fluoropropionamide G-6.

後処理

  1. customevaporated to dryness

出典と根拠

ORDレコード
ord-18765e8d08314601b6d4cede53efec69
出典データセット
uspto-grants-2004_09
特許番号
US06797820B2

反応ノート

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