Benzenesulfonyl chloride → HCID 14858860, compound

HRID 1074001Notes

Reaction equation

HRID 1074001 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:27])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:27])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:26])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:18][S:41]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:43])=[O:42])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13391125HCID 13391125, compound

Product 1

HCID 14858860HCID 14858860, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

L-phenylalanyl-L-proline benzylester hydrochloride (1.94 g, 5 mmole) was dissolved in methylene chloride (30 ml), and triethylamine (1.11 g, 11 mmole) was added thereto at -30° C. Methylene chloride (10 ml) solution of benzene sulfonyl chloride (0.86 g, 5 mmole) was added dropwise to the solution. The mixture was stirred for 1 hour at less than 0° C., and then for 5 hours at room temperature, and methylene chloride (60 ml) was added thereto. The solution was washed with 5% aqueous sodium bicarbonate (100 ml, twice), 1N aqueous hydrochloric acid (100 ml, twice) and water (100 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give N-benzenesulfonyl-L-phenylalanyl-L-proline benzylester (yield: 2.14 g, 86.9%).

Workup

  1. customat -30° C
  2. waitfor 5 hours at room temperature
  3. washThe solution was washed with 5% aqueous sodium bicarbonate (100 ml
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-360c76fd77e74ef6ba24c243d1d16f50
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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