Water → Dimethyl 3-aminopentanedioate

HRID 378132

反応式

HRID 378132 の反応式
O=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+].[BH3-]C#[N:19].[Na+].O>CO>[NH2:19][CH:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 4

HCID 962WaterHCID 74591Dimethyl 3-oxoglutarateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 253304Dimethyl 3-aminopentanedioate収率 44.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Dimethyl 3-ketoglutarate (13 g) in methanol (50 ml) was treated with ammonium formate (5 g) and NaCNBH3 (2 g). 10 ml of H2O was added and the excess solvent removed under reduced pressure. The semi-solid was dissolved in 5% aqueous HCl (250 ml), and washed with CH2Cl2 (2×50 ml). The aqueous layer was made basic (pH>9) with K2CO3 and the product was extracted using CH2Cl2 (2×75 ml). The organic layers were combined and dried with Na2SO4. The excess solvent was removed to give 2.5 g of the dimethyl (±)3-aminoglutarate. This was dissolved in methanol (50 ml) and treated with 4N HCl/Dioxane (10 ml). The excess solvent was removed under reduced pressure to give a 2.7 g of dimethyl (±)3-aminoglutarate hydrochloride. MS and 1H-NMR were consistent with the desired product.

後処理

  1. customthe excess solvent removed under reduced pressure
  2. dissolutionThe semi-solid was dissolved in 5% aqueous HCl (250 ml)
  3. washwashed with CH2Cl2 (2×50 ml)
  4. extractionthe product was extracted
  5. dry with materialdried with Na2SO4
  6. customThe excess solvent was removed

出典と根拠

ORDレコード
ord-75cca8b566924213a2028830e6c65034
出典データセット
uspto-grants-2000_02
特許番号
US06028223

関連ノート

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