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Triphenylphosphine → N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester

HRID 1393367
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HRID 1393367 반응식
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:34])[C@H:16]([CH2:24][C:25]1[CH:30]=[C:29]([I:31])[C:28]([OH:32])=[C:27]([I:33])[CH:26]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].[OH:35][C:36]1[CH:50]=[CH:49][C:39]([O:40][C:41]2[CH:48]=[CH:47][C:44]([CH2:45]O)=[CH:43][CH:42]=2)=[CH:38][CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][O:14][C:15](=[O:34])[C@H:16]([CH2:24][C:25]1[CH:26]=[C:27]([I:33])[C:28]([O:32][CH2:45][C:44]2[CH:47]=[CH:48][C:41]([O:40][C:39]3[CH:49]=[CH:50][C:36]([OH:35])=[CH:37][CH:38]=3)=[CH:42][CH:43]=2)=[C:29]([I:31])[CH:30]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 13941953N-Trifluoroacetyl-3,5-diiodotyrosine methyl esterHCID 230339384-(4-Hydroxyphenoxy)benzylalcohol

생성물 1

HCID 86598312N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diethylazodicarboxylate (40% toluene solution 0.55 ml) was added dropwise to a solution of N-trifluoroacetyl-3,5-diiodo-L-tyrosine methyl ester (272 mg, 0.5 mmol), 4-(4-hydroxyphenoxy)benzylalcohol (119 mg, 0.55 mmol) and triphenylphosphine (328 mg, 1.25 mmol) in tetrahydrofuran (5 ml) under argon atmosphere at −15° C., and the mixture was stirred at the same temperature for 1.5 hrs. The solvent of the reaction mixture was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2) to give N-trifluoroacetyl-O-[4-(4-hydroxy-phenoxy)benzyl]-3,5-diiodo-L-tyrosine methyl ester (280 mg, 76%) as colorless crystals.

후처리

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2)

출처 및 근거

ORD 기록
ord-9ca0397011df4c128cadb1cfcad24497
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345068B2

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