Water → N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77318

반응식

HRID 77318 반응식
[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:28])[CH3:27])[NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][C:23](=[O:25])[CH3:24])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:27])[CH3:28])[N:8]([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][C:23](=[O:25])[CH3:24])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 78911-Bromo-3-methylbutane2회HCID 11430Potassium CarbonateHCID 67155170N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

생성물 1

HCID 67155272N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (3.15 g, 7.48 mmol) in N,N-dimethylformamide (15 mL) is added potassium carbonate (3.09 g, 22.36 mmol), followed by 1-bromo-3-methyl butane (1.79 mL, 14.94 mmol), and the reaction is allowed to stir at ambient temperature for 16 h. Another equivalent of 1-bromo-3-methyl butane (0.9 mL, 7.5 mmol) is added and the reaction is allowed to stir for 16 h at ambient temperature. The reaction is poured over water and extracted three times with dichloromethane. The combined organic extracts are washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by column chromatography and eluted with a gradient of 2-7% (hexanes-ethyl acetate) to afford the title compound as a yellow oil (2.5 g, 68% yield), along with N-isoamyl-N-(6-(3-methylbutoxy)naphthalene-2-sulfonyl)-D-valine tert-butyl ester as a yellow oil (0.3 g, 7.7% yield). LCMS (m/z): (492.26; M+1).

후처리

  1. stirringto stir for 16 h at ambient temperature
  2. extractionextracted three times with dichloromethane
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography
  7. washeluted with a gradient of 2-7% (hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-4536dfcebac34c8ea9fe3b69ded015d4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841291B2

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