Water → 10-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-decanoic acid ethyl ester

HRID 2120704Notes

Reaction equation

HRID 2120704 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH:6]([C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:2].O.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH:6]([C:22]1[CH:27]=[N:26][C:25]([CH3:28])=[N:24][CH:23]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 6966645410-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-dec-4-enoic acid ethyl ester

Product 1

HCID 2062248610-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-decanoic acid ethyl esterYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 24-5 (650 mg, 1.60 mmol), water (100 mg), ammonium formate (512 mg, 8.12 mmol), and 10% palladium on carbon (75 mg) in ethanol (40 mL) was heated to 90 ° C. for 1 hour. The reaction mixture was filtered through celite and the filtrate evaporated in vacuo to afford the title compound 24-6 (600 mg). The crude product was used directly in the next reaction. ESLRMS m/e 408 g/mole (M++H, C22H37N3O4=408 g/mole.)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-727218e2f4f249e69b9a40283e4a1083
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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