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Sodium Bicarbonate → 4-(3'-Fluoro-5'-hydroxymethyl-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

HRID 2066864
ノート
印刷プレビュー

反応式

HRID 2066864 の反応式
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:26]([F:27])=[CH:25][C:24]([CH:28]=[O:29])=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[C:26]([F:27])=[CH:25][C:24]([CH2:28][OH:29])=[CH:23][N:22]=3)[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866550114-(3'-Fluoro-5'-formyl-2,3,5,6-tetrahydro-[1,2]bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

生成物 1

HCID 583336054-(3'-Fluoro-5'-hydroxymethyl-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester収率 44%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

The crude 53b was taken up with methanol (10 mL), cooled in an ice bath and treated with NaBH4 (0.52 g, 13.7 mmol). The mixture was stirred for 2 h and treated with aqueous NaHCO3 (10 mL). The mixture was extracted with 40 mL of ethyl acetate, washed with brine (3×30 mL) and concentrated under vacuum. The residue was purified by flash chromatography (eluent: 20 to 70% ethyl acetate+0.1% triethylamine in hexane) to afford 296 mg (44% yield) of 53-1: LC-MS 409.2 (MH+), tR=5.59 (Method 2). EC50: 224 nM.

後処理

  1. temperaturecooled in an ice bath
  2. extractionThe mixture was extracted with 40 mL of ethyl acetate
  3. washwashed with brine (3×30 mL)
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by flash chromatography (eluent: 20 to 70% ethyl acetate+0.1% triethylamine in hexane)

出典と根拠

ORDレコード
ord-d5a097b7b29e4a918f30c72914af670f
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293729B2

反応ノート

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