Ammonia → HCID 86651606、化合物

HRID 1867330ノート

反応式

HRID 1867330 の反応式
[C:1](Cl)(Cl)=[O:2].[OH:5][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][CH2:20][CH2:21][C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:24])[CH3:23])([CH2:10][CH2:11][CH3:12])[CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.N>C1COCC1.CCOC(C)=O>[C:28]([O:27][C:26](=[O:32])[NH:25][C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][N:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:6]([CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH3:12])[O:5][C:1]1=[O:2])([CH3:30])([CH3:29])[CH3:31]

参加物

7

反応物 4

HCID 222AmmoniaHCID 6371PhosgeneHCID 8471TriethylamineHCID 86600980Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

生成物 1

HCID 86651606HCID 86651606、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

8.85 mL (16.81 mmol) of phosgene solution (20 wt. % in toluene) is slowly added dropwise at 0° C. to a solution of 6.00 g (15.28 mmol) of tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate and 5.32 mL (38.21 mmol) of triethylamine in absolute THF (80 mL). The mixture is stirred for 2 hours at RT, diluted with EtOAc, combined with ice, and made basic with saturated aqueous ammonia solution. The aqueous phase is exhaustively extracted with EtOAc and the combined organic phases are washed with saturated aqueous NaCl, dried with sodium sulfate, and evaporated down in vacuo. After column chromatography (silica gel, cyclohexane/EtOAc 6:1) the product is obtained as a yellow oil. Yield: 4.57 g (71%).

後処理

  1. extractionThe aqueous phase is exhaustively extracted with EtOAc
  2. washthe combined organic phases are washed with saturated aqueous NaCl
  3. dry with materialdried with sodium sulfate
  4. customevaporated down in vacuo
  5. customAfter column chromatography (silica gel, cyclohexane/EtOAc 6:1) the product is obtained as a yellow oil

出典と根拠

ORDレコード
ord-bb40f34fc136417cb756bfccf000e995
出典データセット
uspto-grants-2009_12
特許番号
US07632834B2

反応ノート

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