4-Nitrobenzenesulfonyl chloride → HCID 722228, compound

HRID 1280392Notes

Reaction equation

HRID 1280392 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C1C[O:12]CC1.[OH2:14].C([N:17]([CH2:20][CH3:21])CC)C.[N+]([C:25]1C=C[C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-])=O>ClCCl>[N+:17]([C:20]1[CH:21]=[CH:25][CH:26]=[CH:27][C:28]=1[S:31]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:33])=[O:32])([O-:12])=[O:14]

Participants

6

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 71563D-ValineHCID 21881883Oxolane--water (1/1)

Product 1

HCID 722228HCID 722228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: To a stirred solution of D-valine (10.0 g) in a 2:1 mixture of THF/water (200 mL) containing triethylamine (3 equiv.) at 50° C. is added 4-nitrobenzene-sulfonyl chloride (0.9 equiv.) and the reaction is stirred at room temperature overnight. The resulting mixture is diluted with dichloromethane, and washed with 1N HCl, and water. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to provide the desired N-(nitrobenzenesulfonyl)-(D)-valine as a crude amino acid product. A solution of the crude amino acid (10 grams) in dry toluene (80 mL) is charged with dimethylformamide di-tertbutylacetal (45 mL) and heated to 100° C. for several hours. The resulting cooled solution is concentrated by rotary evaporation and purified by silica gel chromatography to provide the desired N-(4-nitrobenzenesulfonyl)-(D)-valine, tert-butyl ester.

Workup

  1. washwashed with 1N HCl, and water
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89fe39968145487abdb5dd95763978b4
Source dataset
uspto-grants-2002_09
Patent number
US06451791B1

Reaction notes

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