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Tetrabutylammonium Fluoride → {4-[2-Hydroxy-2-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051208
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HRID 1051208 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24](=[O:40])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][Si](C)(C)C)=[C:28]([N+:37]([O-:39])=[O:38])[CH:27]=1)([CH3:22])([CH3:21])[CH3:20].[I:41][C:42]1[C:47]([CH:48]=[O:49])=[C:46]([O:50][CH3:51])[N:45]=[CH:44][CH:43]=1>C1COCC1>[C:19]([O:23][C:24](=[O:40])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH:48]([OH:49])[C:47]2[C:46]([O:50][CH3:51])=[N:45][CH:44]=[CH:43][C:42]=2[I:41])=[C:28]([N+:37]([O-:39])=[O:38])[CH:27]=1)([CH3:22])([CH3:21])[CH3:20]
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5

반응물 3

HCID 2724141Tetrabutylammonium FluorideHCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 90102892HCID 90102892, 화합물

생성물 1

HCID 90102607{4-[2-Hydroxy-2-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The resultant (3-nitro-phenyl)-carbamic acid tert-butyl ester 2 can then be placed into solution with THF and reacted with ((trimethylsilyl)methyl)magnesiumchloride. A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in THF can then be added and allowed to react under conditions known to a skilled artisan to afford (3-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester 3. Tetra-butylammonium fluoride can then be added to a solution of ester 3 and 4-iodo-2-methoxynicotinaldehyde in THF to afford {4-[2-hydroxy-2-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester 4. A solution of compound 4, in turn, can be added to 2,2,2-trifluoroacetic anhydride and allowed to react to afford trifluoro-acetic acid 2-(4-tert-butoxycarbonyl-amino-2-nitro-phenyl)-1-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl ester 5.

출처 및 근거

ORD 기록
ord-1f3ab013999f4cd4a49f97893873d9fa
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09388166B2

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