Methanesulfonyl chloride → HCID 86665967, compound

HRID 1965208Notes

Reaction equation

HRID 1965208 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:15]2[CH:11]([N:12](C(OCC3C=CC=CC=3)=O)[CH2:13][CH:14]2[CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]2[NH:12][CH2:13][CH:14]([CH2:16][O:17][S:38]([CH3:37])(=[O:40])=[O:39])[CH:15]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67606706HCID 67606706, compound

Product 1

HCID 86665967HCID 86665967, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of alcohol 77 (0.78 g, 2.1 mmol) in DCM (12 mL) was cooled to 0° C. and treated with DIPEA (0.55 mL, 3.2 mmol) followed by methanesulfonyl chloride (0.22 mL, 2.8 mmol). After 1 h, the solution was diluted with DCM, washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford mesylate 79 as a light yellow-colored foam which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.36-7.31 (m, 5H), 5.19-5.09 (m, 2H), 4.45 (m, 1H), 4.29-4.04 (m, 3H), 3.71-3.44 (m, 4H), 3.22-3.12 (m, 1H), 2.96 (s, 3H), 2.85-2.70 (m, 1H), 2.21-1.99 (m, 2H), 1.49 (s, 9H) ppm.

Workup

  1. washwashed successively with 1M HCl, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-36916405b574477c9c1909cd797a71a9
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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