Methanesulfonyl chloride → HCID 59315610, compound

HRID 1930509Notes

Reaction equation

HRID 1930509 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:10][CH2:11][OH:12].C(N(C(C)C)C(C)C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:12][CH2:11][CH2:10][CH2:9][C@@H:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[NH:13][C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59315611HCID 59315611, compound2×

Product 1

HCID 59315610HCID 59315610, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(2-bromophenyl)-4-hydroxybutylcarbamate (compound 5; 59.4 mmol, 20.44 g) in dry methylene chloride (500 mL) cooled in an ice bath was added N-ethyldiisopropylamine (119 mmol, 15.35 g) followed by the slow addition of methane sulfonyl chloride (60.0 mmol, 6.87 g) under nitrogen maintaining the reaction temperature below 5° C. Once the addition was complete the cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature and left to stir for two days. The reaction mixture was evaporated at 45° C. under vacuum and residue taken up in methylene chloride (500 mL) washed with 0.5% citric acid, dried over magnesium sulfate with activated charcoal, filtered through a bed of dicalite and evaporated to give a slightly oily solid which was triturated with heptane to give (S)-4-(2-bromophenyl)-4-(tert-butoxycarbonylamino)butyl methanesulfonate 23.25 g) as a pale brown solid, MS (ES): m/z [M+H]+ 422 and 424.

Workup

  1. additionOnce the addition
  2. customwas removed
  3. waitleft
  4. customThe reaction mixture was evaporated at 45° C. under vacuum and residue
  5. washwashed with 0.5% citric acid
  6. dry with materialdried over magnesium sulfate with activated charcoal
  7. filtrationfiltered through a bed of dicalite
  8. customevaporated
  9. customto give a slightly oily solid which
  10. customwas triturated with heptane

Sources & evidence

ORD record
ord-377b73fa7f89432d8817b0cb8798abc1
Source dataset
uspto-grants-2012_05
Patent number
US08188123B2

Reaction notes

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