Acetic Acid → HCID 70137322, compound

HRID 367329Notes

Reaction equation

HRID 367329 reaction equation
C(OC([NH:11][C@H:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:17][CH:18]=2)[CH2:13]1)=O)C1C=CC=CC=1.[H][H].[C:31]([OH:34])(=[O:33])[CH3:32]>[C].[Pd]>[C:31]([OH:34])(=[O:33])[CH3:32].[NH2:11][C@H:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:17][CH:18]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 53809809HCID 53809809, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70137322HCID 70137322, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

(S)-2 -[2-(Benzyloxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (100 mg) and 20 mg of 10% palladium-carbon were suspended in 5 ml of acetic acid and the suspension was stirred at room temperature for 3 hours in an atmosphere of hydrogen. The catalyst was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanoldiethyl ether to give 72 mg of (S)-2-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yloxy)-N,N-dimethylacetamide acetate having a melting point of 135 to 142° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was recrystallized from ethanoldiethyl ether

Sources & evidence

ORD record
ord-7d48ca9d3f5a4935a1491ee77f613d45
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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