(R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester → (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid

HRID 1802958Notes

Reaction equation

HRID 1802958 reaction equation
C([O:8][C:9](=[O:36])[CH2:10][C@@H:11]([NH:16][C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=1)[CH2:12][N:13]([CH3:15])[CH3:14])C1C=CC=CC=1>[Pd]>[F:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[F:33])[CH2:26][O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]([NH:16][C@@H:11]([CH2:12][N:13]([CH3:15])[CH3:14])[CH2:10][C:9]([OH:36])=[O:8])=[O:35]

Participants

3

Reactant 1

HCID 46223509(R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

Product 1

HCID 46223510(R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester (125 mg, 0.25 mmol) was hydrogenated under atmospheric pressure in the presence of palladium (10% on activated charcoal, 30 mg). After 30 min, the catalyst was filtered off and the filtrate concentrated and dried to afford (R)-3-[8-(3,4-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid (96 mg, 89%). Light yellow oil, m/e=413.2 ([M−H]−).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate concentrated
  3. customdried

Sources & evidence

ORD record
ord-d415e5bf950b4f8d98af0666351f25d9
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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