1-Hydroxybenzotriazole → tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

HRID 1912073ノート

反応式

HRID 1912073 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([O-:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN[O:27][CH3:28].C1C=CC2N(O)N=[N:35][C:33]=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:13](=[O:15])[NH:35][CH2:33][O:27][CH3:28])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750434-tert-Butyl 2-(3-benzyloxypropyl)succinate

生成物 1

HCID 71114707tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

4-tert-Butyl 2-(3-benzyloxypropyl)succinate (80 g), triethylamine (48.4 mL) and DMF (400 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (31.5 g), HOBt.H2O (45.6 g) and WSC.HCl (57.1 g) at ice temperature. The mixture was stirred at RT overnight. To the reaction mixture was added water (400 mL), and the mixture was extracted with hexane (480 mL, 480 mL, 240 mL). The combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (84.1 g) as a crude product.

後処理

  1. extractionthe mixture was extracted with hexane (480 mL, 480 mL, 240 mL)
  2. washThe combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-02b0ae7dd9114c44b291f09a85f9c779
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

読み込み中…