4-Morpholinecarbonyl chloride → (2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid

HRID 1516426ノート

反応式

HRID 1516426 の反応式
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:4]2=[CH:3][CH:2]=1.[N:17]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[N:17]1([C:23]([NH:16][C@@H:12]([CH2:11][C:10]2[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH:7]=[CH:8][CH:9]=2)[C:13]([OH:15])=[O:14])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

参加物

5

反応物 2

HCID 848104-Morpholinecarbonyl chlorideHCID 27248831-Naphthyl-L-alanine

生成物 1

HCID 12986165(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid収率 38.1%

試薬・触媒・溶媒 2

HCID 10340Sodium Carbonate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of L-1-naphthylalanine (215 mg, 1 mmol) (Peptech Corp.) in 5 mL 1N NaOH and 0.5 mL saturated Na2CO3 (resulting solution at pH 10) was added morpholine-4-carbonyl chloride (150 mg, 1.0 mmol) dissolved in 5 mL. Afterwards, the reaction mixture was stirred at room temperature for 2 h. The alkaline solution was extracted once with ether (10 mL) and the aqueous phase was acidified with 1N HCl. This was extracted twice with 20 mL EtOAc, and the combined organic phases were washed with 50 mL 1N HCl. The organic phase was dried over Na2SO4, filtered and evaporated to an oil, which solidifies to yields 125 mg (38%) of the desired material. This compound was used as such in the next step.

後処理

  1. dissolutiondissolved in 5 mL
  2. extractionThe alkaline solution was extracted once with ether (10 mL)
  3. extractionThis was extracted twice with 20 mL EtOAc
  4. washthe combined organic phases were washed with 50 mL 1N HCl
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to an oil, which

出典と根拠

ORDレコード
ord-e42da54d6730416389978886b4c043aa
出典データセット
uspto-grants-2012_07
特許番号
US08227450B2

反応ノート

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