Triethylamine → HCID 86749741, compound

HRID 1078521Notes

Reaction equation

HRID 1078521 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-f46f30273b1a4a5f9b11db087d3ea612
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

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