Acetonitrile → tert-butyl glycyl-D-valinate hydrochloride

HRID 254073Notes

Reaction equation

HRID 254073 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][C@@H:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])=O)C1C=CC=CC=1.CC#N.[ClH:30].N1C=CC=CC=1>CCO.[Pd]>[ClH:30].[NH2:11][CH2:12][C:13]([NH:15][C@@H:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10176127Pyridinium chlorideHCID 66843039tert-butyl N-[(benzyloxy)carbonyl]glycyl-D-valinate

Product 1

HCID 86613090tert-butyl glycyl-D-valinate hydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl N-[(benzyloxy)carbonyl]glycyl-D-valinate (3.89 g, 10.7 mmol) and Pd on charcoal (95%, 0.3 g) were mixed in EtOH (95%, 80 ml) and stirred under H2-atmosphere for 2 h. The mixture was filtered through Celite 521 and the solvent was evaporated under reduced pressure. MeCN (25 ml) and pyridine hydrochloride (1.25 g, 10.8 mmol) were added. The solvent was evaporated under reduced pressure to give 2.3 g (81%) of the title product. NMR (500 MHz, CD3COOD) 0.96-1.01 (m, 6H), 1.49 (s, 9H), 2.13-2.23 (m 1H), 3.76 (AB, 2H), 4.28-4.33 (m, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite 521
  2. customthe solvent was evaporated under reduced pressure
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b09358493a0f4e55aa3151d2c0ad9d7e
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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