Triethylamine → 4-Pyridyl-ethanesulfonyl-valine benzyl ester

HRID 265841Notes

Reaction equation

HRID 265841 reaction equation
C1(C)C=C[C:4]([S:7](O)(=[O:9])=[O:8])=[CH:3]C=1.[CH2:12]([O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:27]1[CH:32]=[CH:31][C:30](S(Cl)(=O)=O)=[CH:29][CH:28]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:24])[CH3:25])[N:22]([C:30]1[CH:29]=[CH:28][N:27]=[CH:32][CH:31]=1)[S:7]([CH2:4][CH3:3])(=[O:9])=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11567066O-benzyl-L-valine toluene-p-sulphonateHCID 11586382Pyridine-4-sulfonyl Chloride

Product 1

HCID 700586244-Pyridyl-ethanesulfonyl-valine benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1 gm of valine benzyl ester p-toluene-sulfonic acid salt in 40 ml of CH2Cl2 at 0° C. was added 1.12 gm of 4-pyridylsulfonyl chloride (U.S. Pat. No. 431,504 (1982)) and 1.9 ml of triethylamine. After 1 hour, the solution was washed with water and extracted with CH2Cl2 (2×100 ml), dried and concentrated. Silica gel column chromotography provided 4-pyridyl-ethanesulfonyl-valine benzyl ester which was treated with 10% Pd/C in methanol under hydrogen atmosphere to provide the desired product in 85% overall yield.

Workup

  1. washthe solution was washed with water
  2. extractionextracted with CH2Cl2 (2×100 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c58e0f0973e04885b9308fc986a6b2b4
Source dataset
uspto-grants-1997_07
Patent number
US05648497

Reaction notes

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