Triethylamine → HCID 54089616, compound

HRID 263506Notes

Reaction equation

HRID 263506 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].C(N(CC)CC)C.[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 15747426HCID 15747426, compound

Product 1

HCID 54089616HCID 54089616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of alcohol 15 (1.94 g, 6.81 mmol) and triethylamine (1.25 g, 12.4 mmol) at 0° C. in Cl2CH2 (15 mL), methanesulfonyl chloride (0.96 g, 8.4 mmol) was added. The reaction mixture was allowed to stir at 0° C. for 20 min. It was 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 removed in vacuo and the crude mesylate 16 was obtained as a foamy white solid, which was used in the next step without further purification. 1H NMR (CDCl3).δ1.394 (s, 9H), 2.916 (s, 3H), 3.718 (s, 3H), 4.878 (dd, J=8.7, 5.0 Hz, 1H, H-2), 5.231 (bd, J=8.7 Hz, 1H, H--N), 5.917 (d, J =5.0 Hz, 1H, H-3), 7.379-7.425 (m, 5H).

Workup

  1. customIt was 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
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-66359badf9c24f259f4e2a4970487d99
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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