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

HRID 912892

Reaction equation

HRID 912892 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-5de44db36eea43b2b9e94ed22a6f09a2
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Linked notes

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