Hydrochloric Acid → HCID 59755951, compound

HRID 1360342Notes

Reaction equation

HRID 1360342 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15][CH2:14]2)[CH2:9]1)C1C=CC=CC=1.Cl.N#N>CCO.[Pd]>[NH:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:14][CH2:15][S:16](=[O:20])(=[O:19])[CH2:17][CH2:18]2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 59756032HCID 59756032, compound

Product 1

HCID 59755951HCID 59755951, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound Y (88 mg, 0.2989 mmol, 1 eq) was dissolved in EtOH (2.0 ml) and 1N HCl was added (300 μl). Degassed solution 3 times with N2 and the Palladium catalyst (10 mg, 5% mmol) was added. Degassed with H2 (g) 3 times and hydrogenated for 90 minutes. The catalyst was filtered off and 1N HCl was added (300 μl). The solvent was removed in vacuo and taken up in water and lyophilized to obtain the desired compound as a yellow oil (59 mg, 82%). 1H NMR (400 MHz) D2O δ 3.88-3.68 (dm, 2H), 3.57-3.45 (m, 10H), 3.37-3.29 (m, 2H), 2.45 (m, 1H), 2.10 (m, 1H). 205.1 [M+H]+.

Workup

  1. customDegassed with H2 (g) 3 times and hydrogenated for 90 minutes
  2. filtrationThe catalyst was filtered off
  3. addition1N HCl was added (300 μl)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-77eb31ef69fc46b2ac04ef1ffc08dc13
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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