Water → HCID 14010105, compound

HRID 1788783Notes

Reaction equation

HRID 1788783 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]([O:16][C:17]([NH:19][CH:20]1[C:23]([CH3:25])([CH3:24])[N:22]([OH:26])[C:21]1=[O:27])=[O:18])([CH3:15])([CH3:14])[CH3:13].O>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:21]([N+:6]([CH2:7][CH2:13][CH2:12][CH3:14])([CH2:11][CH2:10][CH2:9][CH3:8])[CH2:25][CH2:23][CH2:20][CH3:21])[CH2:20][CH2:23][CH3:24].[S:2]([O-:5])([O:26][N:22]1[C:23]([CH3:25])([CH3:24])[CH:20]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[C:21]1=[O:27])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24638Chlorosulfonic acidHCID 14010103HCID 14010103, compound

Product 1

HCID 14010105HCID 14010105, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of chlorosulfonic acid (12.27 g, 0.105 mole) in 210 ml of dichloromethane at -40° C. under argon was treated with 20.5 g (0.26 mole) of pyridine dropwise over 10 minutes. The mixture is stirred for 10 more minutes at 0° C. and 10 minutes at 25° C. A slurry of (±)-3-[(t-butyloxycarbonyl)amino]-1-hydroxy-4,4-dimethyl-2-azetidinone in 20 ml of dichloromethane was added and the mixture stirred at 25° C. for 3.5 hours. The nearly homogenous solution was then treated with 250 ml of water and 17 g (0.05 mole) of tetrabutylammonium hydrogen sulfate. The mixture was mixed well and the organic layer separated and dried over sodium sulfate. Evaporation in vacuo gave a foam, which was purified further by dissolution in ethyl acetate, removing insolubles, and evaporation to the title compound as a foam, 30 g.

Workup

  1. stirringthe mixture stirred at 25° C. for 3.5 hours
  2. additionThe mixture was mixed well
  3. customthe organic layer separated
  4. dry with materialdried over sodium sulfate
  5. customEvaporation in vacuo
  6. customgave a foam, which
  7. customwas purified further by dissolution in ethyl acetate
  8. customremoving
  9. custominsolubles, and evaporation to the title compound as a foam, 30 g

Sources & evidence

ORD record
ord-372b48998a944947acdc316bd1e13103
Source dataset
uspto-grants-1987_08
Patent number
US04684722

Reaction notes

Loading…