Triethylamine → HCID 57068580, compound

HRID 654318Notes

Reaction equation

HRID 654318 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([OH:13])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.CCOCC>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([O:13][S:26]([CH3:25])(=[O:28])=[O:27])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10514391HCID 10514391, compound

Product 1

HCID 57068580HCID 57068580, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.29 g (1.19 mmol) of the resultant compound of Example 31 and 0.25 ml (1.8 mmol) of triethylamine in 7 ml of dichloromethane was cooled to 0° C. and treated with 0.12 ml (1.55 mmol) of methanesulfonyl chloride. After 45 min, the solution was diluted with ether, washed sequentially with 10% aqueous citric acid, aqueous NaHCO3 and saturated brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using 3:1 hexane:ethyl acetate provided 0.23 g (61%) of the desired compound (Rf 0.48, 3:2 hexane:ethyl acetate).

Workup

  1. washwashed sequentially with 10% aqueous citric acid, aqueous NaHCO3 and saturated brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ecdcd291e94aefaa1622d9b80e2554
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

Loading…