Methanesulfonyl chloride → HCID 10379776, compound

HRID 1822468Notes

Reaction equation

HRID 1822468 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH2:13][OH:14])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[CH2:13][O:14][S:26]([CH3:25])(=[O:28])=[O:27])=[O:15])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 7018766Boc-L-leucinol

Product 1

HCID 10379776HCID 10379776, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((1S)-1-hydroxymethyl-3-methyl-butyl)-carbamic acid tert-butyl ester (25 g, 115 mmol) in dichloromethane (500 ml) cooled by an ice-water bath was successively added diisopropylethylamine (35.7 g, 276 mmol) and methanesulphonyl chloride (15.81 g, 138 mmol). The resulting solution was stirred over night during which time the mixture was allowed to gradually warm up to ambient temperature. The mixture was washed successively with water, 10% citric acid (aq), water and saturated NaHCO3 (aq), then dried with Na2SO4 and concentrated to a brown solid (32.6 g, 96%) which was used in the next reaction without further purification.

Workup

  1. washThe mixture was washed successively with water, 10% citric acid (aq), water and saturated NaHCO3 (aq)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated to a brown solid (32.6 g, 96%) which
  4. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-4e5f09e6c67043dda0ea480e259d6860
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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