Hydrochloric Acid → HCID 86753930, compound

HRID 1418621Notes

Reaction equation

HRID 1418621 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6](CC1C=CC=CC=1)[CH2:7][CH2:8][C@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])#[N:2].Cl>C(O)C.[Pd]>[C:1]([CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10617529HCID 10617529, compound

Product 1

HCID 86753930HCID 86753930, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

21 g (60.8.10-3 mol) of [3-[(3-cyanopropyl)(phenylmethyl)amino]-1-(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester are dissolved in 400 ml of ethanol, and 0.25 ml of 10M hydrochloric acid is then added, followed by 1.2 g of 5% palladium on charcoal. The mixture is stirred under a hydrogen atmosphere at room temperature and at atmospheric pressure. After a reaction time of 24 hours, the catalyst is filtered off and the filtrate is then concentrated under reduced pressure. The residue is purified by chromatography on silica gel using an ethyl acetate/ethanol/aqueous ammonia mixture (6/3/0.1 v/v) as the eluent to give 6 g of the expected product in the form of an oil (yield=34%).

Workup

  1. filtrationAfter a reaction time of 24 hours, the catalyst is filtered off
  2. concentrationthe filtrate is then concentrated under reduced pressure
  3. customThe residue is purified by chromatography on silica gel using an ethyl acetate/ethanol/aqueous ammonia mixture (6/3/0.1 v/v) as the eluent

Sources & evidence

ORD record
ord-91497d7949f34c128ca87b8fae357147
Source dataset
uspto-grants-1999_03
Patent number
US05883132

Reaction notes

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