Triethylamine → HCID 54089615, compound

HRID 263504Notes

Reaction equation

HRID 263504 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:14]([S:30]([CH3:29])(=[O:32])=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10935304HCID 10935304, compound

Product 1

HCID 54089615HCID 54089615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of alcohol 4 (0.94 g, 3.18 mmol) and NEt3 (0.73 g, 7.18 mmol) at 0° C. in Cl2CH2 (10 mL), methanesulfonyl chloride (418 mg, 3.65 mmol) was added. The reaction mixture was allowed to stir at 0° C. for 45 min. It was then quenched with cold dilute HCl, diluted with Cl2CH2 and the organic layer was washed with an aqueous solution of NaHCO3 followed by brine and dried over Na2SO4. The solvent was eliminated in vacuo and the crude mesylate 6 was obtained as a foamy white solid which was used in the next step without further purification. 1H NMR (CDCl3).δ1.417 (s, 9H), 2.910 (s, 3H, CH3 --OMs), 3.705 (s, 3H, CH3O--), 4.853 (dd, J=9.6, 6.6 Hz, 1H, H--C2), 5.173 (bd, J=9.6 Hz, 1H, H--N), 5.893 (d, J=6.6 Hz, 1H, H--C3), 7.389-7.400 (m, 5H); IR (KBR) 3400, 2980, 2950, 1745, 1715, 1520, 1360, 1180 cm-1.

Workup

  1. customIt was then quenched with cold dilute HCl
  2. additiondiluted with Cl2CH2
  3. washthe organic layer was washed with an aqueous solution of NaHCO3
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-23a03903118b486b9ce9e47eb6c9a3a4
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

Loading…