DL-leucine → HCID 3140382, compound

HRID 1767671Notes

Reaction equation

HRID 1767671 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[OH-].[Na+].[NH2:16][CH:17]([C:22]([OH:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20]>O>[CH3:20][CH:19]([CH3:21])[CH2:18][CH:17]([NH:16][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 857DL-leucineHCID 14798Sodium Hydroxide2×HCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 3140382HCID 3140382, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-nitrobenzenesulfonylchloride (11 g; 50 mmol) and NaOH (2.1 g; 53 mmol) in H2O (100 ml) was added DL-leucine (6.55 g; 50 mmol) and left over night with stirring at rt. The reaction mixture was added 4 M NaOH (12.5 ml) and filtered. The filtrate was acidified with 1 M HCl (50 ml) and extracted with EtOAc. The combined organic fractions were dried (Na2SO4) and evaporated to dryness to give 6.7 g (42%) product.

Workup

  1. waitleft over night
  2. filtrationfiltered
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f3c64ee24b2d4579b2250ee99e8a1987
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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