Sodium Hydroxide → HCID 19700602, compound

HRID 1488682Notes

Reaction equation

HRID 1488682 reaction equation
[Sn](Cl)Cl.[CH2:4]([O:6][C:7](=[O:32])[CH2:8][CH2:9][NH:10][C:11](=[O:31])[C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:13]=1[N+:28]([O-])=O)[CH3:5].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(OCC)(=O)C.C(O)C.C(OCC)(=O)C>[CH2:4]([O:6][C:7](=[O:32])[CH2:8][CH2:9][NH:10][C:11](=[O:31])[C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=2)[CH:15]=[CH:14][C:13]=1[NH2:28])[CH3:5]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 22905326HCID 22905326, compound

Product 1

HCID 19700602HCID 19700602, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
70 °C

Procedure

Tin(II) chloride (12.2 g, 64.4 mmol) was added to a solution of 5.12 g (12.9 mmol) of N-(5-(4-cyanobenzyloxy)-2-nitrobenzoyl)-b-alanine ethyl ester in 40 mL of 1:1 ethyl acetate/ethanol and the mixture heated to 70° C. for 15 min, cooled, and poured into a mixture of ice water, 1N sodium bicarbonate, and ethyl acetate. 1N sodium hydroxide was added carefully until a clear solution resulted and the aqueous phase was separated and extracted with ethyl acetate. The combined organics were washed with water, brine, dried over anhydrous magnesium sulfate, and concentrated to give a dark solid that was purified by chromatography (silica gel-60, 1:1 ethyl acetate/hexane) to give 2.51 g (53%) of N-(5-(4-cyanobenzyloxy)-2-aminobenzoyl)-b-alanine ethyl ester as a light yellow solid. 1H NMR (300 MHz, CDCl3) d 7.67 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.52 (2H, d, J=8.3 Hz, NC-Ar-H2), 6.94 (1H, d, J=2.9 Hz, O-Ar-H), 6.89 (1H, dd, J=2.9, 8.8 Hz, O-Ar-H), 6.78 (1H, b, N-H), 6.66 (1H, d, J=8.8 Hz, O-Ar-H), 5.04 (2H, s, ArCH2O), 4.16 (2H, q, J=7.3 Hz, OCH2CH3), 3.66 (2H, bq, J=5.8 Hz, NHCH2CH2), 2.62 (2H, t, J=5.8 Hz, NHCH2CH2), 1.27 (3H, t, J=7.3 Hz, OCH2CH3); Exact mass (FAB, M+H+) calcd for C20 H22N3O4 : 368.1610; Found: 368.1603.

Workup

  1. temperaturecooled
  2. customresulted
  3. customthe aqueous phase was separated
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a dark solid
  9. customthat was purified by chromatography (silica gel-60, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7dd0eb3535634cd48170356097563eec
Source dataset
uspto-grants-1997_10
Patent number
US05674865

Reaction notes

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