Triethylamine → HCID 54402299, compound

HRID 2259518Notes

Reaction equation

HRID 2259518 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C@@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]4[N:27]=[C:26]5[C:28]([Cl:32])=[C:29]([Cl:31])[S:30][C:25]5=[CH:24][CH:23]=4)[CH:15]=3)[OH:13])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C([O-])(O)=O.[Na+]>>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C@@H:12]([C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]4[N:27]=[C:26]5[C:28]([Cl:32])=[C:29]([Cl:31])[S:30][C:25]5=[CH:24][CH:23]=4)[CH:17]=[CH:18][CH:19]=3)[O:13][S:41]([CH3:40])(=[O:43])=[O:42])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 54574910HCID 54574910, compound

Product 1

HCID 54402299HCID 54402299, compound

Conditions

Temperature
0 °C

Procedure

To a solution of the alcohol (Step 5) (230 mg, 0.47 mmol) in CHCl2 (2.5 mL) was added at -40° C. Et3N (100 μL, 0.717 mmol) and MsCl (45.0 μL, 0.574 mmo.). The resulting mixture was then warmed to 0° C. After a period of 10 min, a saturated solution of NaHCO3 was added. The mesylate was extracted with CH2C12, dried over Na2SO4, evaporated and co-distilled two times with toluene and used as such for the next step.

Workup

  1. extractionThe mesylate was extracted with CH2C12
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-2d4410c0ad994e30a806dc25e70c9589
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

Loading…