HCID 131727888, compound → HCID 131727887, compound

HRID 1444556Notes

Reaction equation

HRID 1444556 reaction equation
C([O:8][CH2:9][C@H:10]([C:12]([N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[OH:15])=[O:13])[NH2:11])C1C=CC=CC=1>CCO.[Pd]>[C:19]([O:18][C:16]([N:14]([C:12](=[O:13])[C@@H:10]([CH2:9][OH:8])[NH2:11])[OH:15])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 131727888HCID 131727888, compound

Product 1

HCID 131727887HCID 131727887, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 20 (137 mg, 0.44 mmol) in EtOH (7 mL) containing 10% Pd—C (46 mg) was hydrogenated at 1 atm (1.5 h). The catalyst was filtered and the filtrate was concentrated in vacuo, and then crystallized with isopropyl ether to afford 21 as a solid. Yield, 81%; Rf=0.19 (10% MeOH—CHCl3); mp 108-110° C. (lit.6) mp 106-112° C. for L-isomer); IR (KBr) 3421, 3318, 2871, 1726, 1670, 1514, 1370, 1243, 1160 cm−1; 1H NMR (CD3OD, 300 MHz) δ1.44 (s, 9H), 3.69 (d, J=5.4 Hz, 2H), 4.06 (t, J=5.4 Hz, 1H); 13C NMR (CD3OD, 75 MHz) δ28.7 (3 C), 56.1, 63.2, 80.9, 157.6, 170.1; MS (+CI) 221 [M+1]+; Mr (+CI) 221.113 90 [M+1]+ (calcd for C8H17N2O5, 221.113 74).

Workup

  1. customwas hydrogenated at 1 atm (1.5 h)
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customcrystallized with isopropyl ether

Sources & evidence

ORD record
ord-0c3bad66a70b4094baa4c8689c706d6e
Source dataset
uspto-grants-2010_02
Patent number
US07662856B2

Reaction notes

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