Acetic Acid → HCID 68413846, compound

HRID 1662073Notes

Reaction equation

HRID 1662073 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:27]([NH:29][C@H:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C:35]([O:37]CC(=O)C1C=CC=CC=1)=[O:36])=[O:28])[NH:16][C:17]([C:19]1[N:20]([CH3:26])[C:21]([CH3:25])=[C:22]([CH3:24])[CH:23]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C(O)(=O)C>[Zn].C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:27]([NH:29][C@H:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C:35]([OH:37])=[O:36])=[O:28])[NH:16][C:17]([C:19]1[N:20]([CH3:26])[C:21]([CH3:25])=[C:22]([CH3:24])[CH:23]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 68411906HCID 68411906, compound

Product 1

HCID 68413846HCID 68413846, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-oxo-2-phenylethyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1,4,5-trimethyl-1H-pyrrol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.30 g) and DMF (3.0 ml) were added zinc (0.61 g) and acetic acid (3.0 ml) under ice-cooling, followed by stirring at room temperature for 6 hours. To the reaction mixture was added ethyl acetate and the insolubles were separated by filtration through Celite. The filtrate was concentrated under reduced pressure, and a 1 M aqueous sodium hydroxide solution was added to the residue, followed by washing with diethyl ether. Citric acid was added thereto under ice-cooling, and the solid precipitated was collected by filtration and washed with water to obtain (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1,4,5-trimethyl-1H-pyrrol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylic acid (0.19 g).

Workup

  1. temperaturecooling
  2. customthe insolubles were separated by filtration through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additiona 1 M aqueous sodium hydroxide solution was added to the residue
  5. washby washing with diethyl ether
  6. additionCitric acid was added
  7. temperatureunder ice-cooling
  8. customthe solid precipitated
  9. filtrationwas collected by filtration
  10. washwashed with water

Sources & evidence

ORD record
ord-1387daea585245c49ac689dd7b7324be
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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