Methanesulfonyl chloride → HCID 86647426, compound

HRID 2071035Notes

Reaction equation

HRID 2071035 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.N1C=CC=CC=1>[CH3:20][S:21]([O:1][C:2]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[C:4]([CH2:5][NH:6][C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:13])[CH:3]=1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68671331HCID 68671331, compound

Product 1

HCID 86647426HCID 86647426, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 91.8 mg of tert-butyl 3-hydroxy-5-isopropylbenzylcarbamate in 3 mL of CH2Cl2 and 300 μL of pyridine at 0° C. was added 30 μL (0.386 mmol) of MsCl. The ice bath was removed, and after stirring at r.t. for 75 min. 50 μL of Et3N was added. After 30 min., the solution was concentrated and EtOAc and H2O were added. The organic layer was washed with 15 mL of brine, and the aqueous layer was extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (40% EtOAc/hexanes) provided 96.2 mg of 3-((tert-butoxycarbonylamino)methyl)-5-isopropylphenyl methanesulfonate as a pale yellow oil in about 80% yield.

Workup

  1. customThe ice bath was removed
  2. addition50 μL of Et3N was added
  3. waitAfter 30 min.
  4. concentrationthe solution was concentrated
  5. additionEtOAc and H2O were added
  6. washThe organic layer was washed with 15 mL of brine
  7. extractionthe aqueous layer was extracted with EtOAc
  8. dry with materialThe combined extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash silica gel chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6044d5fed5f640bd95d8f095106aa0ed
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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