Benzyl 3-[5-(3-{[(benzyloxy)carbonyl]amino}prop-1-ynyl)pyridin-2-yl]prop-2-ynylcarbamate → HCID 9813017, compound

HRID 49575Notes

Reaction equation

HRID 49575 reaction equation
C(OC([NH:11][CH2:12][C:13]#[C:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]#[C:22][CH2:23][NH:24]C(=O)OCC2C=CC=CC=2)=[N:19][CH:20]=1)=O)C1C=CC=CC=1.[H][H]>CO>[NH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][NH2:24])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 11453795Benzyl 3-[5-(3-{[(benzyloxy)carbonyl]amino}prop-1-ynyl)pyridin-2-yl]prop-2-ynylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 9813017HCID 9813017, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,5-di(3-benzyloxycarbonylaminoprop-1-ynyl)pyridine (8-1) (8.0 g) in methanol (160 mL) was hydrogenated under 20 psi of hydrogen gas pressure in the presence of 5%-Pd/Al2O3 (1.1 g) for 16 hours. The catalyst was filtered through Solka-flok and washed with methanol. The filtrate and wash were combined and concentrated under reduced pressure to give 12-1 (3.56 g) as a crystalline compound; m.p. 116-119° C.

Workup

  1. filtrationThe catalyst was filtered through Solka-flok
  2. washwashed with methanol
  3. washThe filtrate and wash
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97b8056a109b4282b9f8180fad634aa2
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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