Sodium Hydroxide → HCID 19700602、化合物

HRID 1376652ノート

反応式

HRID 1376652 の反応式
[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]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 22905326HCID 22905326、化合物

生成物 1

HCID 19700602HCID 19700602、化合物収率 53%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21584252Ethanol ethylacetate溶媒

反応条件

温度
70 °C

実験手順

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 C20H22N3O4 : 368.1610; Found: 368.1603.

後処理

  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)

出典と根拠

ORDレコード
ord-b9f0899ffc114f088047c0894273bd66
出典データセット
uspto-grants-1997_09
特許番号
US05663166

反応ノート

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