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tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate → tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

HRID 1689525
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HRID 1689525 반응식
[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][OH:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:46])([CH3:48])[CH3:47])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 57989031tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate

생성물 1

HCID 57989227tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매2회
HCID 6344
Dichloromethane
용매

실험 절차

tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate (Example 276, step g) (0.609 g) was dissolved in dichloromethane (30 mL), treated with manganese (IV) oxide (0.791 g) and the resulting suspension stirred at room temperature over a weekend. More manganese (IV) oxide (0.801 g) was added and the suspension was stirred for a further 4 hours. The mixture was filtered through diatomaceous earth, washing the residue well with DCM, and the combined filtrate and washings were concentrated in vacuo to afford the subtitled compound. Yield 0.521 g. Material used immediately in the next step.

후처리

  1. stirringthe suspension was stirred for a further 4 hours
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washwashing the residue well with DCM
  4. concentrationthe combined filtrate and washings were concentrated in vacuo

출처 및 근거

ORD 기록
ord-29de80bede1243d2b2ab702d2a2a0c76
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08148373B2

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