Methanesulfonyl chloride → HCID 86645839, compound

HRID 1253739Notes

Reaction equation

HRID 1253739 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:18][CH2:19][OH:20])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]1.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>C(Cl)Cl.O>[CH3:24][S:21]([O:1][CH2:2][CH2:3][C:4]1([CH2:18][CH2:19][O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:6][CH2:5]1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66701174HCID 66701174, compound

Product 1

HCID 86645839HCID 86645839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

TEA (1.1 ml, 8.36 mmol, 3.0 eq.) was added to a cooled solution of tert-butyl 4,4-bis(2-hydroxyethyl)azepane-1-carboxylate (800 mg, 2.78 mmol, 1.0 eq.) in methylene chloride (10 ml) at 0° C. and then mesylchloride (0.47 ml, 6.13 mmol, 2.2 eq.) was added to the reaction mixture and it was stirred at RT for 2 h. After completion (monitored by TLC), the reaction mixture was diluted with water (20 ml) and methylene chloride (100 ml). The organic part was separated and the water layer was extracted with methylene chloride (2×20 ml). The combined organic layers were washed with brine (20 ml), dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was used in the next step without further purification.

Workup

  1. customThe organic part was separated
  2. extractionthe water layer was extracted with methylene chloride (2×20 ml)
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-625409ce29454bd7bea6d999a5d69c60
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

Loading…