Sodium Carbonate → HCID 15434756, compound

HRID 1600885Notes

Reaction equation

HRID 1600885 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH:6]([NH2:17])[CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([CH2:7][CH:6]2[NH:17][C:3](=[O:2])[CH2:4][CH2:5]2)=[CH:9]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 15434755HCID 15434755, compound

Product 1

HCID 15434756HCID 15434756, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.5 g (0.10.1 mM) of 4-Amino-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-pentanoic acid methyl ester was dissolved in 20 mL of ethyl acetate. To this solution was added 20 mL of 1N sodium carbonate, and the mixture was stirred at room temperature for 6 hours. The ethyl acetate layer was dried and evaporated. The residue was chromatographed on silica using 95:5 CHCl3 :CH3OH to yield 1.48 g of product as a white crystalline solid. MP=160-162° C. NMR (CDCl3) δ11.4 (s, 1H), 8.05 (m, 1H), 7.85 (d, 1H), 7.45 (s, 1H), 7.18 (s, 1H), 6.95 (m, 1H), 4.0 (m, 1H), 2.8-3.0 (m, 2H), 2.2-2.4 (m, 3H), 1.85 (m, 1H). 13C NMR (CDCl3) 178.6,148.9, 142.4, 127.0, 123.6, 120.1, 115.3, 109.8, 55.2, 32.6, 30.3, 26.8. Mass Spectrum: m/e=216 (p+1).

Workup

  1. dry with materialThe ethyl acetate layer was dried
  2. customevaporated
  3. customThe residue was chromatographed on silica using 95:5 CHCl3

Sources & evidence

ORD record
ord-848b5225c90648b496a46bd04f516535
Source dataset
uspto-grants-1999_11
Patent number
US05977131

Reaction notes

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