Methanesulfonyl chloride → HCID 86689214, compound

HRID 594949Notes

Reaction equation

HRID 594949 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]2)[CH:8]1[C:22]([O:24][CH3:25])=[O:23].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][S:2]([O:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:9]([CH2:10][CH2:11]2)[CH:8]1[C:22]([O:24][CH3:25])=[O:23])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66687992HCID 66687992, compound

Product 1

HCID 86689214HCID 86689214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (1.2 g, 10.6 mmol) was added dropwise to a solution of 8-tert-butyl 2-methyl 3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (5.29 mmol) and diisopropylethylamine (3.42 g, 26.5 mmol) in dichloromethane (25 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 16 h. Dichloromethane (50 ml) was added and washed with saturated sodium bicarbonate solution (50 ml) and brine solution (50 ml). The organic layer was separated, and dried over sodium sulfate. The solution was filtered, concentrated, and used in the next step without further purification.

Workup

  1. washwashed with saturated sodium bicarbonate solution (50 ml) and brine solution (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-3e9a1cbd10864a3489535a379bb89e6c
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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