Citric Acid → N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77317Notes

Reaction equation

HRID 77317 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:21]=[CH:20]2)(=[O:15])[CH3:14].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O>[C:1]([O:5][C:6](=[O:12])[C@@H:7]([CH:9]([CH3:10])[CH3:11])[NH:8][S:27]([C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([O:16][C:13](=[O:15])[CH3:14])[CH:18]=2)[CH:23]=1)(=[O:29])=[O:28])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 6931638tert-butyl D-valinateHCID 19080946HCID 19080946, compound

Product 1

HCID 67155170N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

D-valine tert-butyl ester (6.24 g, 35.9 mmol), 6-acetoxy naphthalene-2-sulfonyl chloride (10.2 g, 35.9 mmol) and triethylamine (12.5 mL, 89.7 mmol) are stirred in dioxane-water (1:1, 243 mL) at ambient temperature for 2 hours. The reaction mixture is acidified with a solution of aqueous citric acid (10% w/w, 800 mL). The precipitate is collected by filtration affording product as pale yellow crystals (10.2 g, 68% yield). LCMS (m/z): (439.28; M+18, 420.24; M−1).

Workup

  1. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-2656ed357bf9411096dae4ec6650ee33
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Reaction notes

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