Carbon Dioxide → HCID 131717782, compound

HRID 2082238Notes

Reaction equation

HRID 2082238 reaction equation
Cl.[NH2:2][C@H:3]([C:7]([NH:9][C@@H:10]([C:23]([NH:25][C@H:26]([C:34]([N:36]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:37])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH:21]=[O:22])[CH:13]=1)=[O:8])[C@@H:4]([CH3:6])[OH:5].ClS([N:49]=[C:50]=[O:51])(=O)=O.C(=O)=O.C(=O)([O-])O.[Na+]>C(#N)C.O.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>[NH2:2][C@:3]([N:49]=[C:50]=[O:51])([C:7]([NH:9][C@@H:10]([C:23]([NH:25][C@H:26]([C:34]([N:36]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH3:37])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH:21]=[O:22])[CH:13]=1)=[O:8])[C@@H:4]([CH3:6])[OH:5]

Participants

10

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 70918Chlorosulfonyl isocyanate2×HCID 516892Sodium BicarbonateHCID 101632290HCID 101632290, compound

Product 1

HCID 131717782HCID 131717782, compoundYield 63.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of HCl.H-Thr-D-Trp(CHO)-Phe-NMeBzl (0.94 g) and triethylamine (0.153 g) in acetonitrile (12 ml), was added chlorosulfonyl isocyanate (0.214 g) under cooling with Dry ice and carbon tetrachloride bath. The solution was stirred at the same temperature for an hour and then stirred under ice-cooling. Chlorosulfonyl isocyanate (0.214 g) was added at this temperature, after stirring for fifteen minutes, water (3 ml) was added. The pH was adjusted to pH 4 with sodium hydrogencarbonate and the mixture was stirred for an hour. After evaporation of acetonitrile, the product was extracted with ethyl acetate under saturation with sodium chloride. The organic layer was washed with sodium chloride solution and concentrated. The residue was dissolved in CH3CN-H2O (8:2) (20 ml) and applied to a column of ®TOYO PEARL HW-40 (26 mmφ, 400 ml) and eluted with CH3CH-H2O (7:3), and fractionated. The main fraction was collected, and after evaporation of acetonitrile, n-butanol and ethyl acetate was added and the organic layer was separated and concentrated to give H2NCO-Thr-D-Trp(CHO)-Phe-NMeBzl (600 mg).

Workup

  1. stirringstirred under ice-
  2. temperaturecooling
  3. stirringafter stirring for fifteen minutes
  4. stirringthe mixture was stirred for an hour
  5. customAfter evaporation of acetonitrile
  6. extractionthe product was extracted with ethyl acetate under saturation with sodium chloride
  7. washThe organic layer was washed with sodium chloride solution
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in CH3CN-H2O (8:2) (20 ml)
  10. wash(26 mmφ, 400 ml) and eluted with CH3CH-H2O (7:3)
  11. customThe main fraction was collected
  12. customafter evaporation of acetonitrile, n-butanol and ethyl acetate
  13. additionwas added
  14. customthe organic layer was separated
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-898423fb821e4524ae82edfdf8358f34
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

Loading…