1,2-Dichloroethane → HCID 9797912, compound

HRID 1707329Notes

Reaction equation

HRID 1707329 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=O)[CH2:3][SH:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:23]([NH:31][C:32](=[O:39])[C@H:33]([C@H:35]([CH2:37][CH3:38])[CH3:36])[NH2:34])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:23]([NH:31][C:32](=[O:39])[C@H:33]([C@H:35]([CH2:37][CH3:38])[CH3:36])[NH:34][C:5](=[O:7])[C@H:2]([CH2:3][SH:4])[NH2:1])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 5862L-(+)-CysteineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 18655292HCID 18655292, compound

Product 1

HCID 9797912HCID 9797912, compoundYield 168.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(t-Butoxycarbonyl)-S-triphenylmethyl)-L-cysteine (0.26 g, 0.55 mmol) was dissolved in DMF (3 mL) with EDC (0.11 g, 0.55 mmol), HOBT (0.074 g, 0.55 mmol) and L-isoleucine-phenethylamide hydrochloride (0.135 g, 0.5 mmol) at .ambient temperature. The pH of the solution was adjusted to 6.5 with triethylamine (0.15 mL, 1.05 mmol). After stirring for 16 h the solvent was evaporated and the residue was partitioned between EtOAc (20 mL) and H20 (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organic extract was washed with 10% citric acid solution, aqueous saturated NaHCO3 solution, brine, and dried (Na2SO4). Filtration and concentration gave 0.285 g (87%) of the title compound after chromatography (SiO2, EtOAc: hexane, 1:2).

Workup

  1. customambient temperature
  2. customwas evaporated
  3. customthe residue was partitioned between EtOAc (20 mL) and H20 (20 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. extractionThe combined organic extract
  6. washwas washed with 10% citric acid solution, aqueous saturated NaHCO3 solution, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-f0ec6202bbff42cf93953c3e50e7cc7f
Source dataset
uspto-grants-1994_10
Patent number
US05352705

Reaction notes

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