Diethylamine → HCID 53811186, compound

HRID 651110Notes

Reaction equation

HRID 651110 reaction equation
C(NCC)C.[C:6]([O:10][C:11](=[O:41])[CH2:12][C@H:13]([NH:23]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:14]([N:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1)=[O:15])([CH3:9])([CH3:8])[CH3:7]>CN(C)C=O>[C:6]([O:10][C:11](=[O:41])[CH2:12][C@H:13]([NH2:23])[C:14]([N:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1)=[O:15])([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54448861HCID 54448861, compound

Product 1

HCID 53811186HCID 53811186, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethylamine (1.0 mmol) was added to (S)-3-(9H-fluoren-9-ylmethoxycarbonyl-amino)-4-(4-hydroxy-piperidin-1-yl)-4-oxo-butyric acid tert-butyl ester in dimethyl-formamide (5 ml) at 25° C. After 1 hour, the reaction mixture was concentrated, the residue suspended in 1:1 ether/dichloromethane, filtered and concentrated. The residue was purified by chromatography on silica gel eluted with 1-50% ethanol in dichloromethane containing 0.5% ammonium hydroxide. Yield 217 mg, 80%.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel
  5. washeluted with 1-50% ethanol in dichloromethane containing 0.5% ammonium hydroxide

Sources & evidence

ORD record
ord-eb0fb7cc590c4a769ae38cb3057cac49
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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