Sodium Hydroxide → HCID 131723794, compound

HRID 1861630Notes

Reaction equation

HRID 1861630 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+].[CH2:18]([S:25](Cl)(=[O:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH2:18]([S:25]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])(=[O:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 74740Phenylmethanesulfonyl chloride2×HCID 248202386-tert-Butoxy-6-oxo-L-norleucine

Product 1

HCID 131723794HCID 131723794, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 0.5 g of H-Aad(OtBu)-OH in 4.4 mL of aqueous 1 N sodium hydroxide was added 0.42 g of benzylsulfonylchloride in 2 mL of dioxane. After 16 hours at room temperature, additional 1.4 mL of aqueous 2 N sodium hydroxide, 0.5 mL of dioxane and 0.09 g of benzylsulfonylchloride were added and the reaction mixture stirred for an additional day. The dioxane was removed, water was added, the mixture made acid (pH 3) using hydrochloric acid and extracted twice with diethyl ether. The combined ether layers were dried over sodium sulfate and concentrated to give 235 mg of BzlSO2-Aad(OtBu)-OH.

Workup

  1. customThe dioxane was removed
  2. additionwater was added
  3. extractionextracted twice with diethyl ether
  4. dry with materialThe combined ether layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c7d8f534edc4006835e668ac7386090
Source dataset
uspto-grants-2003_03
Patent number
US06534495B1

Reaction notes

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