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Diisopropylcarbodiimide → Tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

HRID 1170551
ノート
印刷プレビュー

反応式

HRID 1170551 の反応式
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:21]([C:25](O)=[O:26])[CH:22]([CH3:24])[CH3:23].CC(C)N=C=NC(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]1([C:7]2([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:25]([CH:21]([NH:20][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH:22]([CH3:24])[CH3:23])=[O:26])=[CH:17][CH:18]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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 3

HCID 12734DiisopropylcarbodiimideHCID 83693Boc-L-ValineHCID 15384544-(1-Phenylcyclohexyl)phenol

生成物 1

HCID 66967822Tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 8028
Tetrahydrofuran
溶媒
3 回

実験手順

To a stirred solution at room temperature of 4-(1-phenylcyclohexyl)phenol (311 mg, 1.23 mmol) in dry THF (2 mL) was added BocValOH (295 mg, 1.36 mmol) dissolved in THF (2 mL). A solution of DIC (231 μL; 1.48 mmol) in THF (2 mL) was added drop wise, which caused precipitation after a few minutes. After 5 min DMAP (166 mg; 1.36 mmol) was added and stirring was continued for 19 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (eluent: EtOAc (0-10%) in heptane) affording 517 mg (1.14 mmol; 93%) of colourless oil. LC-MS purity (UV/MS): 100/100%, Rt 6.77 min, M+18: 469.53.

後処理

  1. customprecipitation after a few minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography (eluent: EtOAc (0-10%) in heptane)
  4. customaffording 517 mg (1.14 mmol; 93%) of colourless oil

出典と根拠

ORDレコード
ord-199f4c55933f43cdb1c99f4faed311db
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07825265B2

反応ノート

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