Hydrochloric Acid → 3-[3-(6-Amino-pyridin-3-yl)-2-ethoxycarbonyl-propyldisulfanyl]-2-(6-amino-pyridin-3-ylmethyl)-propionic acid ethyl ester

HRID 1789922Notes

Reaction equation

HRID 1789922 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:47])[CH:6]([CH2:32][C:33]1[CH:34]=[N:35][C:36]([NH:39]C(OC(C)(C)C)=O)=[CH:37][CH:38]=1)[CH2:7][S:8][S:9][CH2:10][CH:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:12][C:13]1[CH:14]=[N:15][C:16]([NH:19]C(OC(C)(C)C)=O)=[CH:17][CH:18]=1)[CH3:3]>C(OC(=O)C)C>[CH2:30]([O:29][C:27](=[O:28])[CH:11]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([NH2:19])=[CH:17][CH:18]=1)[CH2:10][S:9][S:8][CH2:7][CH:6]([C:5]([O:4][CH2:2][CH3:3])=[O:47])[CH2:32][C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[CH:37][CH:38]=1)[CH3:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53842374HCID 53842374, compound

Product 1

HCID 867601233-[3-(6-Amino-pyridin-3-yl)-2-ethoxycarbonyl-propyldisulfanyl]-2-(6-amino-pyridin-3-ylmethyl)-propionic acid ethyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Etylacetate saturated with HCl (g) (15 mL) was added to a solution of 3-[3-(6tert-butoxycarbonylamino-pyridin-3-yl)-2-ethoxycarbonyl-propyldisulfanyl]-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-propionic acid ethyl ester (130 mg, 0.191 mmol) in ethylacetate (7 mL) at 0° C. The reaction was allowed to attain room temperature and was stirred for 19 h, then evaporated under reduced pressure. The residue was dissolved in water, saturated aqueous Na2CO3 was added and the aqueous phase was extracted with CH2Cl2. The organic layer was dried and concentrated under reduced pressure to give the title compound (90 mg, 98%).

Workup

  1. customto attain room temperature
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. additionsaturated aqueous Na2CO3 was added
  5. extractionthe aqueous phase was extracted with CH2Cl2
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72e6ad47645f40be8af30f229f1b433d
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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