Acetic Acid → HCID 136085211, compound

HRID 1893209Notes

Reaction equation

HRID 1893209 reaction equation
C([O:8][CH2:9][C@@H:10]([O:36][CH3:37])[CH2:11][CH2:12][CH:13]([C:24]1[NH:25][C:26](=[O:35])[C:27]([OH:34])=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=1)[N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH3:16])C1C=CC=CC=1.C(O)(=O)C>CCOC(C)=O.CO.[Pd]>[C:20]([O:19][C:17]([N:14]([CH2:15][CH3:16])[CH:13]([C:24]1[NH:25][C:26](=[O:35])[C:27]([OH:34])=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=1)[CH2:12][CH2:11][C@H:10]([O:36][CH3:37])[CH2:9][OH:8])=[O:18])([CH3:22])([CH3:23])[CH3:21]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 136085214HCID 136085214, compound

Product 1

HCID 136085211HCID 136085211, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-{(4S)-5-(benzyloxy)-1-[(tert-butoxycarbonyl)(ethyl)amino]-4-methoxypentyl}-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (13 g, 25.02 mmol) in EtOAc (30 mL) and MeOH (30 mL) was added acetic acid (20 mL) and palladium on carbon (Degussa, 10% by mass, 13 g, 122 mmol). The reaction mixture was shaken on a Parr apparatus under hydrogen gas (50 psi) for 4 days and then filtrated through a pad of celite. The filter cake was washed with MeOH. The filtrate was concentrated in vacuo. The crude residue was used in the next reaction without further purification. LC-MS: 429.89 (M+1).

Workup

  1. filtrationfiltrated through a pad of celite
  2. washThe filter cake was washed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-0b8711295a96493a83559e8cae8f0a1a
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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