Methanesulfonyl chloride → HCID 86614671, compound

HRID 1433773Notes

Reaction equation

HRID 1433773 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][OH:14])=[CH:7][CH:6]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68620241HCID 68620241, compound

Product 1

HCID 86614671HCID 86614671, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (R)-tert-butoxycarbonylamino-[4-(2-hydroxy-ethoxy)-phenyl]-acetic acid methyl ester (80 mg, 0.25 mmol) in pyridine (1.5 mL) was added methanesulfonyl chloride (0.023 mL, 0.30 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. The solvent was evaporated and the crude product was purified by chromatography over silica gel eluted with 3:1 v/v hexanes/ethyl acetate to give (R)-tert-butoxycarbonylamino-[4-(2-methanesulfonyloxy-ethoxy)-phenyl]-acetic acid methyl ester (50 mg, 50% yield) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by chromatography over silica gel
  3. washeluted with 3:1 v/v hexanes/ethyl acetate

Sources & evidence

ORD record
ord-78aab84673e24498b1f4d867d6b26b9c
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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