Lithium borohydride → HCID 21072811、化合物

HRID 1867340ノート

反応式

HRID 1867340 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20](=[O:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]1[C:36]2[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=2[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]1=[O:46].[BH4-].[Li+]>C1COCC1.O.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH2:21][NH:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]2[C:36]3[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=3[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]2=[O:46])[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 4148881Lithium borohydrideHCID 21072818HCID 21072818、化合物HCID 22063474HCID 22063474、化合物

生成物 1

HCID 21072811HCID 21072811、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

A solution of 232 mg (0.649 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 200 mg (0.649 mmol) of 1-(3-amino-3-methylbutyl)-4,4-diethyl-7-fluoro-1,4-dihydrobenzo[d][1,3]oxazin-2-one in absolute THF (5 mL) is stirred for 2.5 hours at RT. The mixture is cooled to 5° C., combined with 60 mg (2.755 mmol) lithium borohydride, heated to RT, and stirred for 1 hour. The mixture is again cooled to 5° C. and slowly diluted with 15 mL of water and 20 mL of dichloromethane. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried with sodium sulfate and concentrated by evaporation in vacuo. The residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5). Yield: 257 mg (65%); HPLC-MS: Rt=16.5 min. (method A).

後処理

  1. temperatureheated to RT
  2. temperatureThe mixture is again cooled to 5° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried with sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5)

出典と根拠

ORDレコード
ord-cc756705ac364bc0a3a81f70287e5fd8
出典データセット
uspto-grants-2009_12
特許番号
US07632834B2

反応ノート

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