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

HRID 77318

Reaction equation

HRID 77318 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 78911-Bromo-3-methylbutane2×HCID 11430Potassium CarbonateHCID 67155170N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4536dfcebac34c8ea9fe3b69ded015d4
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Linked notes

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