Dichloromethane → N-benzyl-O-benzyl-D-serinamide

HRID 534679

反応式

HRID 534679 の反応式
[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.FC(F)(F)C(O)=O.[OH-].[Na+]>O>[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

生成物 1

HCID 67082833N-benzyl-O-benzyl-D-serinamide収率 90.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (30 g) and dichloromethane (150 mL), trifluoroacetic acid (150 mL) was added. The solution was stirred for 2 hours at room temperature for completion of reaction. The solution was concentrated under vacuum to obtain solid which was dissolved in water. The aqueous layer was basified to pH 8-10 with 5% sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue solidify by n-Hexane to give 20 g of N-benzyl-O-benzyl-D-serinamide.

後処理

  1. concentrationThe solution was concentrated under vacuum
  2. customto obtain solid which
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with brine solution
  5. concentrationOrganic layer was concentrated under vacuum
  6. customto obtain an oily residue solidify by n-Hexane

出典と根拠

ORDレコード
ord-be2f9f7a3be14f24980bc1a11043ee1e
出典データセット
uspto-grants-2014_10
特許番号
US08853439B2

関連ノート

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