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Triphenylphosphine → 3,5-dichloro-N-trifluoroacetyl-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine methyl ester

HRID 1393369
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HRID 1393369 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]([Cl:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].[C:35]1([C:41]2[O:42][C:43]3[C:49]([CH2:50]O)=[CH:48][CH:47]=[CH:46][C:44]=3[N:45]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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]([Cl:33])[C:28]([O:32][CH2:50][C:49]2[C:43]3[O:42][C:41]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:45][C:44]=3[CH:46]=[CH:47][CH:48]=2)=[C:29]([Cl: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 150239503,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl esterHCID 199399197-Hydroxymethyl-2-phenyl-benzoxazole

생성물 1

HCID 865983133,5-dichloro-N-trifluoroacetyl-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine methyl ester수율 82%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

Diethylazodicarboxylate (40% toluene solution 0.63 ml) was added dropwise to a solution of 3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (252 mg, 0.7 mmol), [(2-phenyl)-benzoxazol-7-yl]methanol (193 mg, 0.857 mmol) and triphenylphosphine (374 mg, 1.43 mmol) in tetrahydrofuran (3 ml) under argon atmosphere at 5° C., and the mixture was stirred at the same temperature for 60 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=4) to give 3,5-dichloro-N-trifluoroacetyl-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine methyl ester (324 mg, 82%) 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=4)

출처 및 근거

ORD 기록
ord-d31440fd74bb47fd8ddc7d12eae66813
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345068B2

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