HCID 54210448, compound → HCID 53842374, compound

HRID 1789921Notes

Reaction equation

HRID 1789921 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([CH2:11][C:12]1[CH:13]=[N:14][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:16][CH:17]=1)[CH2:6][S:7]C(=O)C)[CH3:2]>C(O)C.N>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([CH2:11][C:12]1[CH:13]=[N:14][C:15]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[CH:16][CH:17]=1)[CH2:6][S:7][S:7][CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:26])[CH2:11][C:12]1[CH:13]=[N:14][C:15]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[CH:16][CH:17]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54210448HCID 54210448, compound

Product 1

HCID 53842374HCID 53842374, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

3-Acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-propionic acid ethyl ester (150 mg, 0.392 mmol) was dissolved in ethanol (15 mL) saturated with NH3 (g). After stirring for 160 min., the mixture was concentrated under reduced pressure. The residue was dissolved in EtOH (10 mL) whereafter a solution of 12 in EtOH (0.5 M, 0.784 mL) was added. The reaction was stirred for 30 min. at room temperature, then diluted with CH2Cl2, washed with saturated aqueous Na2S2O5 and saturated aqueous NaHCO3, dried, filtered and concentrated under reduced pressure to give 3-[3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-ethoxycarbonyl-propyldisulfanyl]-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-propionic acid ethyl ester (130 mg, 98%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOH (10 mL) whereafter a solution of 12 in EtOH (0.5 M, 0.784 mL)
  3. additionwas added
  4. stirringThe reaction was stirred for 30 min. at room temperature
  5. additiondiluted with CH2Cl2
  6. washwashed with saturated aqueous Na2S2O5 and saturated aqueous NaHCO3
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d892903084fa44d4a6cbbfbe8d170525
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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