Methanesulfonyl chloride → ((2(5)-Benzoylamino-3-methylbutyryl)-(3-methanesulfonylbenzyl)amino)acetic Acid Ethyl Ester

HRID 1456673Notes

Reaction equation

HRID 1456673 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]([C:15](=[O:29])[C@@H:16]([NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](N)[CH:9]=1)[CH3:2].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1.CCOC(C)=O.Cl>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]([C:15](=[O:29])[C@@H:16]([NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S:32]([CH3:31])(=[O:34])=[O:33])[CH:9]=1)[CH3:2]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54307894((2(S)-Benzoylamino-3-methylbutyryl)-(3-aminobenzyl)amino)acetic Acid Ethyl Ester

Product 1

HCID 53767326((2(5)-Benzoylamino-3-methylbutyryl)-(3-methanesulfonylbenzyl)amino)acetic Acid Ethyl EsterYield 99.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 735 (476.0 mg, 1.16 mmol) in pyridine (3.0 mL) was added methanesulfonyl chloride (135 μL, 1.75 mmol), and the reaction allowed to stir overnight. The reaction was diluted with EtOAc and 1N HCl. The layers were separated and the organic phase washed with brine, dried over MgSO4, filtered and concentrated to provide 550 mg of 744. ##STR123##

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2795cb816aa641caa4cbd6b87d0d97c1
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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