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Phenol → Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate

HRID 1036696
ノート
印刷プレビュー

反応式

HRID 1036696 の反応式
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5]([N:7]1[CH2:24][CH2:23][CH2:22][C@:9]2([C:13](=[O:14])[N:12]([CH3:15])[CH2:11][C@H:10]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8]1)=[O:6].[C:33]1(O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:15][N:12]1[CH2:11][C@@H:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@:9]2([CH2:22][CH2:23][CH2:24][N:7]([C:5](=[O:6])[C@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:3][CH2:2][O:1][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:8]2)[C:13]1=[O:14]
参加物反応条件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 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86674099tert-butyl (R)-4-hydroxy-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxobutan-2-ylcarbamate

生成物 1

HCID 86674100Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Tert-butyl (R)-4-hydroxy-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxobutan-2-ylcarbamate (111 mg; 0.249 mmol) was solubilised in THF (2.5 ml). Phenol (24 mg; 0.249 mmol) was added followed by triphenylphosphine (98 mg; 0.374 mmol). The solution was cooled to 0° C. and diisopropyl azodicarboxylate (0.073 ml; 0.374 mmol) was added. The reaction mixture was warmed to RT slowly and stirred overnight. The solution was concentrated in vacuo and purified by chromatography on silica eluting with 0-10% MeOH in DCM with ammonia. The compound eluted with triphenylphospine oxide and was used crude in the next step.

後処理

  1. temperatureThe reaction mixture was warmed to RT slowly
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by chromatography on silica eluting with 0-10% MeOH in DCM with ammonia
  4. washThe compound eluted with triphenylphospine oxide

出典と根拠

ORDレコード
ord-1583e359f7194d4f86c26c11106c47ce
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546416B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート