Methanesulfonyl chloride → HCID 86757203, compound

HRID 1386916Notes

Reaction equation

HRID 1386916 reaction equation
[CH3:1][O:2][C:3]1[C@H:4]([C@@H:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:15][CH2:16][OH:17])[N:5]=[C:6]([O:12][CH3:13])[C@@H:7]([CH:9]([CH3:11])[CH3:10])[N:8]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(C(C)C)CC)(C)C>ClCCl.CCOCC>[CH3:1][O:2][C:3]1[C@H:4]([C@@H:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:15][CH2:16][O:17][S:27]([CH3:26])(=[O:29])=[O:28])[N:5]=[C:6]([O:12][CH3:13])[C@@H:7]([CH:9]([CH3:10])[CH3:11])[N:8]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69624833HCID 69624833, compound

Product 1

HCID 86757203HCID 86757203, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above oil 3(R)-[(2S,5R)-2,5-dihydro-3,6-dimethoxy-5-(1-methylethyl)-2-pyrazinyl]-3-(4-methoxyphenyl)propanol (28) (17.7 g) was dissolved in 300 mL of dichloromethane. To the solution at −5° C. was added methane sulfonyl chloride (8.02 g, 5.42 mL, 70 mmol) followed by diisopropylethylamine (DIPEA, 12 mL, 70 mmol) dropwise over 10 min. The reaction was stirred at 0° C. for 2 hour. The light yellow solution was diluted with 2 L of ether and was washed with water (3×200 mL) and brine (2×200 mL). After it was dried over sodium sulfate, the solution was concentrated to a volume of 160 mL under vacuum at 20° C. TLC in EA/H (=1:1): Rf=0.74, as a major spot; Rf=0.21, as a minor spot.

Workup

  1. washwas washed with water (3×200 mL) and brine (2×200 mL)
  2. dry with materialAfter it was dried over sodium sulfate
  3. concentrationthe solution was concentrated to a volume of 160 mL under vacuum at 20° C

Sources & evidence

ORD record
ord-8b58181b4a8643fc8b7f4a56d1812bde
Source dataset
uspto-grants-2001_07
Patent number
US06265572B1

Reaction notes

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