Triethylamine → HCID 86749741, compound

HRID 1940647Notes

Reaction equation

HRID 1940647 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:36][S:37]([O:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68453819HCID 68453819, compound

Product 1

HCID 86749741HCID 86749741, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.88 g(7.28 mmol) of the alcohol 2 in 32 mL dichloromethane at 0° C. was treated with 1.29 g(1.77 mL, 12.7 mmol) of triethylamine followed by addition of 1.04 g(0.70 mL, 9.10 mmol) of methanesulfonylchloride. The solution was stirred at 0° C. for 15 min, followed by dilution with dichloromethane and extraction with water. The solution was dried (Na2SO4) and concentrated in vacuo to afford 3.4 g(98%) of the mesylate 3 as a light pink solid (high resolution mass spectrum: calcd for C20H28FN3O7S: 473.1632. found: 473.1631), sufficiently pure for use in the next step.

Workup

  1. extractionfollowed by dilution with dichloromethane and extraction with water
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e7353f8a50348bfa8541952f0b9ce65
Source dataset
uspto-grants-1997_12
Patent number
US05700799

Reaction notes

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