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

HRID 860096Notes

Reaction equation

HRID 860096 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.

Workup

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

Sources & evidence

ORD record
ord-c6be5f02f9364cae97f62771de34e5ed
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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