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

HRID 1393369
ノート
印刷プレビュー

反応式

HRID 1393369 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 150239503,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl esterHCID 199399197-Hydroxymethyl-2-phenyl-benzoxazole

生成物 1

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

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d31440fd74bb47fd8ddc7d12eae66813
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07345068B2

反応ノート

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