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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

HRID 16371
ノート
印刷プレビュー

反応式

HRID 16371 の反応式
[CH2:1]([O:8][C@H:9]([CH3:25])[C@H:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][O:12][CH2:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:29]([CH2:33]C)C(C)C)(C)C.Cl.CN[O:38][CH3:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:21]([O:20][C:18](=[O:19])[NH:17][C@H:10]([CH2:11][O:12][CH2:13][C:14](=[O:16])[NH:29][CH2:33][O:38][CH3:39])[C@H:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:25])([CH3:24])([CH3:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 67373378((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid

生成物 1

HCID 67379173
{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of ((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid (42.1 g) in DMF (400 mL) was successively added N,N-diisopropylethylamine (41 mL), N,O-dimethylhydroxyamine hydrochloride (17.4 g), EDCI (34.3 g) and HOBt (24.1 g), and the resultant solution was stirred for 16 hours at room temperature. Solvent was removed by distillation under reduced pressure, and the resultant product was diluted with ethyl acetate and water. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure. After passing the residue through a silica pad (silica gel 500 cc), the filtrate was concentrated by distillation under reduced pressure, to thereby obtain the titled compound (46.0 g). The physical properties of the compound were as follows.

後処理

  1. customSolvent was removed by distillation under reduced pressure
  2. additionthe resultant product was diluted with ethyl acetate and water
  3. customThe organic layer was partitioned
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customSolvent was removed by distillation under reduced pressure
  7. concentrationthe filtrate was concentrated by distillation under reduced pressure

出典と根拠

ORDレコード
ord-6acb6780b90244fb9f07bbaa5a2fe621
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737141B2

反応ノート

読み込み中…

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