Pyridine → HCID 15330044, compound

HRID 1063904Notes

Reaction equation

HRID 1063904 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[OH:13][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].N1C=CC=CC=1>ClCCl>[C:8]([O:12][C:6]([NH:5][S:2]([O:13][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20])(=[O:4])=[O:3])=[O:7])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 15330044HCID 15330044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To chlorosulfonylisocyanate (10.3 g) was added t-butyl alcohol (6.96 ml) in dichloromethane (30 ml) under ice-water cooling and the mixture was stirred at ambient temperature for 0.5 hour. The solution was added into a mixture of N-hydroxysuccinimide (8.38 g) and pyridine (6.47 ml) in dichloromethane (150 ml) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. The solution was washed with 0.1N hydrochloric acid, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (200:1, 100:1, 200:3, 50:1) to give N-(t-butoxycarbonylamino-sulfonyloxy)succinimide as colorless oil (2.93 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. washThe solution was washed with 0.1N hydrochloric acid, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a mixture of chloroform and methanol (200:1, 100:1, 200:3, 50:1)

Sources & evidence

ORD record
ord-4e65ef7ebc2b4930837b75e7958a5eaa
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

Loading…