Triethylamine → HCID 53822454, compound

HRID 2413727Notes

Reaction equation

HRID 2413727 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:28])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:27])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37]>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:28])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:27])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:26])[C@H:23]([CH3:25])[NH:24][S:38]([CH2:36][CH3:37])(=[O:40])=[O:39])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 22827652HCID 22827652, compound

Product 1

HCID 53822454HCID 53822454, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

L-alanyl-L-prolyl-L-proline benzylester hydrochloride (4.09 g, 10.0 m mole) was added to methylene dichloride (40 ml) and triethyl amine (2.02 g, 20.0 m mole), was added thereto while stirring and cooling with ice. After that, ethanesulfonyl chloride (1.29 g, 10.0 m mole)-methylene dichloride (10 ml) solution was added dropwise over 1 hour thereto. The reaction solution was allowed to stand overnight at room temperature and then washed with two 20 ml portions of hydrochloric acid, 10% aqueous sodium chloride (20 ml), two 20 ml portions of 10% aqueous sodium bicarbonate and 10% aqueous sodium chloride (20 ml) in order. A methylene dichloride layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give a syrupy N-ethanesulfonyl-L-alanyl-L-prolyl-L-proline benzylester (3.85 g).

Workup

  1. additionwas added
  2. temperaturecooling with ice
  3. washwashed with two 20 ml portions of hydrochloric acid, 10% aqueous sodium chloride (20 ml), two 20 ml portions of 10% aqueous sodium bicarbonate and 10% aqueous sodium chloride (20 ml) in order
  4. dry with materialA methylene dichloride layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9b7217a3068846a0a8074dd42912301f
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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