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Ammonium Chloride → Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

HRID 503910
Notes
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Reaction equation

HRID 503910 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]([O:10][C:11](=[O:26])[NH:12][CH2:13][CH:14]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[CH3:25])[CH2:15][CH2:16][OH:17])([CH3:9])([CH3:8])[CH3:7].[NH4+].[Cl-]>C(Cl)Cl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH:14]([CH2:13][NH:12][C:11]([O:10][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:26])[CH2:15][CH2:16][O:17][S:1]([CH3:4])(=[O:3])=[O:2])=[C:19]([CH3:25])[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 66877268[2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 86621498Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
-78 °C

Procedure

Mesyl chloride (7.53 mL, 0.09726 mol) was added, at −78° C., to a solution of [2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester (30.3 g, 0.08457 mol) in DCM (600 mL) followed by TEA (27 mL, 0.1945 mol). The reaction mixture was stirred at −78° C. for 1 hour, then allowed to reach room temperature with stirring for an additional hour. A saturated aqueous solution of NH4Cl was added, and the resulting mixture was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and evaporated under reduced pressure to give methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester, which was used without further purification.

Workup

  1. customto reach room temperature
  2. stirringwith stirring for an additional hour
  3. extractionthe resulting mixture was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-102b2e1bb456495982465ca71248e3b6
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776910B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes