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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
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인쇄 미리보기

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HRID 2066864 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d5a097b7b29e4a918f30c72914af670f
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08293729B2

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