Triethylamine → 4-(Tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate

HRID 423074Notes

Reaction equation

HRID 423074 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:15][CH2:16][OH:17])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:17][CH2:16][CH2:15][CH2:14][CH:13]([NH:18][C:19]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:25])[C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57750417Tert-butyl 1-(4-chlorophenyl)-4-hydroxybutylcarbamate2×

Product 1

HCID 577503184-(Tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.511 mL, 6.60 mmol) was added dropwise to tert-butyl 1-(4-chlorophenyl)-4-hydroxybutylcarbamate (Intermediate 55) (1.80 g, 6.00 mmol) and triethylamine (1.004 mL, 7.20 mmol) in DCM (30.0 mL) at 25° C. over a period of 15 minutes under nitrogen. The resulting solution was stirred at room temperature for 30 minutes. The resulting mixture was evaporated to dryness and the residue was suspended in DCM, filtered and the filtrate purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate (2.270 g, 100%) as a white solid.

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. filtrationfiltered
  3. customthe filtrate purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in isohexane
  4. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-fd7bb5926b124d5e8819920888da0c34
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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