Triethylamine → tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate

HRID 927378ノート

反応式

HRID 927378 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:19].F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNC>CN(C=O)C.O>[CH3:17][N:18]([CH3:19])[C:10]([C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 151085042-(((Tert-butoxy)carbonyl)amino)-2-ethylbutanoic acid

生成物 1

HCID 86674741tert-Butyl 3-(dimethylcarbamoyl)pentan-3-ylcarbamate収率 53.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-(tert-butoxycarbonylamino)-2-ethylbutanoic acid ((200 mg, 0.87 mmol), HATU (CAN 148893-10-1, 660 mg, 1.74 mmol) and triethylamine (CAN 121-44-8, 260 mg, 2.61 mmol) was added to a solution of dimethylamine hydrochloride (CAN 506-59-2, 117 mg, 1.74 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature. The mixture was added to water (20 mL) and extracted with ethyl acetate (30 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether) to give the product (120 mg, 53.7%); MS (EI): m/e=259.2 [M+H]+

後処理

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by prep-HPLC (eluting with 30% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-b508e1b93e154accaf61316c1fd42050
出典データセット
uspto-grants-2016_03
特許番号
US09290451B2

反応ノート

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