Triethylamine → ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester

HRID 446947ノート

反応式

HRID 446947 の反応式
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[CH2:18]([N:20](CC)[CH2:21]C)C.Cl.CNC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:5]([O:4][C:2](=[O:3])[NH:9][C@@H:10]([C:15](=[O:17])[N:20]([CH3:21])[CH3:18])[CH2:11][CH:12]([CH3:14])[CH3:13])([CH3:8])([CH3:7])[CH3:6]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2724699PyBOPHCID 2724763D-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-, monohydrate

生成物 1

HCID 28165661((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester収率 58%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of Boc-D-leucine monohydrate (2.0 g, 8.0 mmol), triethylamine (5.6 mL, 40.1 mmol), and dimethylamine hydrochloride (1.31 g, 16.0 mmol) in DMF (15 mL) at room temperature was added PyBOP (4.59 g, 8.82 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1) to give 1.19 g (58%) of ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester as a colorless viscous oil.

後処理

  1. washwashed with water (4×50 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated under vacuum
  4. customThe crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1)

出典と根拠

ORDレコード
ord-948d16f949124e3abb92073d9e0fda0f
出典データセット
uspto-grants-2013_07
特許番号
US08481541B2

反応ノート

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