Acetic Acid → 4-[4-((2S)-2-Amino-2-tert-butoxycarbonyl-ethylamino)-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-butyric acid ethyl ester

HRID 854253Notes

Reaction equation

HRID 854253 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:38])[N:15]=[C:16]([NH:17][CH2:18][C@H:19]([NH:27]C(OCC3C=CC=CC=3)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:11]=2[CH:10]=[CH:9]1)[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:38])[N:15]=[C:16]([NH:17][CH2:18][C@H:19]([NH2:27])[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C:11]=2[CH:10]=[CH:9]1)[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 15546709HCID 15546709, compound

Product 1

HCID 155467104-[4-((2S)-2-Amino-2-tert-butoxycarbonyl-ethylamino)-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-butyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

709 mg of 4-[4-((2S)-2-benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-butyric acid ethyl ester were dissolved in 40 ml of ethanol and 1 ml of acetic acid and were hydrogenated over 100 mg of Pd/C (10%) during 4 h at room temperature. The catalyst was removed by filtration, the solvent was removed in vacuo. The residue was dissolved in 60 ml of DCM and stirred with 10 ml of brine and additional 5 g of NaHCO3. The phases were separated, the aqueous phase was extracted with DCM, the combined organic phases were dried over MgSO4, filtered and the solvent was removed in vacuo. Yield: 475 mg.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 60 ml of DCM
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with DCM
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f3ddb532bd5841d6b8015cf926dc63ea
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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