HCID 86744569, compound → HCID 67830825, compound

HRID 1708877Notes

Reaction equation

HRID 1708877 reaction equation
C(OC([NH:11][C:12]([C@H:14]1[C@@H:17]([C:18]([NH2:20])=[O:19])[CH2:16][NH:15]1)=[O:13])=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH:15]1[CH2:16][C@H:17]([C:18]([NH2:20])=[O:19])[C@@H:14]1[C:12]([NH2:11])=[O:13]

Participants

5

Reactant 2

HCID 86744569HCID 86744569, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67830825HCID 67830825, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of cis-N-(Benzyloxycarbonyl) azetidine 2,3-dicarboxylic acid and, e.g., ammonia are reacted with [(CH3)2N]3PCl2 to form the cis-N(benzyloxycarbonyl)azetidine-2,3-dicarboxamide (XI), as set forth by Appel et al., Chem. Ber. 116, 2037-2040 (1983). XI, 10% Pd/C and methanol are hydrogenated in a Parr shaker under 3 atm of hydrogen, for 4 hours. The catalyst is filtered off and thoroughly washed. The solution is evaporated to dryness and dried in vacuo to arrive at cis-azetidine-2,3-dicarboxamide.

Workup

  1. filtrationThe catalyst is filtered off
  2. washthoroughly washed
  3. customThe solution is evaporated to dryness
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ad6f3563222c49a0948480dc4816d912
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

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