HCID 59752248, compound → HCID 59752171, compound

HRID 750390Notes

Reaction equation

HRID 750390 reaction equation
[OH:1][CH:2]([C@@H:14]([NH:19][C:20]([O:22][CH:23]1[C:27]([CH3:29])([CH3:28])[CH2:26][N:25](C(OCC2C=CC=CC=2)=O)[C:24]1=[O:40])=[O:21])[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6]>O1CCCC1.[Pd]>[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:21])[O:22][CH:23]1[C:27]([CH3:29])([CH3:28])[CH2:26][NH:25][C:24]1=[O:40])[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:6]

Participants

4

Reactant 1

HCID 59752248HCID 59752248, compound

Product 1

HCID 59752171HCID 59752171, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 120 mg (0.22 mmol) of benzyl 3-[({[(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentyl]amino}carbonyl)oxy]-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate in 5 mL of tetrahydrofuran was stirred in the presence of 15 mg of 10% Pd/C under a hydrogen atmosphere (50 psi) for 18 h. The catalyst was filtered off over celite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 3:2 acetone:dichloromethane to afford 60 mg (66%) of 4,4-dimethyl-2-oxo-3-pyrrolidinyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate. ES-LCMS m/z 420 (M+H).

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 3:2 acetone

Sources & evidence

ORD record
ord-6f773de168d54afe84fa672aad99de3f
Source dataset
uspto-grants-2008_07
Patent number
US07402606B2

Reaction notes

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