Dichloromethane piperidine → (3R)-3-Butyl-2,5-piperazinedione

HRID 730833

Reaction equation

HRID 730833 reaction equation
C1C2C(COC([NH:18][C@@H:19]([C:24]([NH:26][CH2:27][C:28]([O:30]C)=O)=[O:25])[CH2:20][CH2:21][CH2:22][CH3:23])=O)C3C(=CC=CC=3)C=2C=CC=1.ClCCl.N1CCCCC1>ClCCl>[CH2:20]([C@H:19]1[NH:18][C:28](=[O:30])[CH2:27][NH:26][C:24]1=[O:25])[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 67144590Dichloromethane piperidineHCID 67401200Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate

Product 1

HCID 67400830(3R)-3-Butyl-2,5-piperazinedione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate from step (a) above (2 g, 4.7 mmol) in a 7:3 mixture of dichloromethane/piperidine (30 mL) was stirred at room temperature for 0.75 h. The reaction mixture was diluted with dichloromethane (200 mL) and solid which precipitated was filtered, washed with cold DCM (2×50 mL) and dried in vacuo to give the title compound as a white solid. MS (ESI, positive ion) m/z: 171 (M+1).

Workup

  1. customprecipitated
  2. filtrationwas filtered
  3. washwashed with cold DCM (2×50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4c5de376c51f4c09b22f26f2de526a00
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Linked notes

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