1-Hydroxybenzotriazole → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

HRID 1912050ノート

反応式

HRID 1912050 の反応式
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:22]([O-:24])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN[O:36][CH3:37].C1C=CC2N(O)N=[N:44][C:42]=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C.C(N(CC)CC)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:22](=[O:24])[NH:44][CH2:42][O:36][CH3:37])[CH2:25][C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[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 866750344-tert-Butyl 2-[2-(tert-butyldiphenylsilanyloxy)ethyl]succinate

生成物 1

HCID 71114767tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

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-[2-(tert-butyldiphenylsilanyloxy)ethyl]succinate (437.4 g), triethylamine (171 mL) and DMF (2000 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (111 g), HOBt.H2O (161 g) and WSC.HCl (201 g) at ice temperature. After stirring at RT overnight, water (800 mL) was poured into the reaction mixture and the mixture was extracted with hexane (2.4 L). The organic layer was washed with water (1.2 L) and 10 w/v % saline solution (1.2 L). The aqueous layer was extracted with hexane (2.4 L) once again and the combined organic layer was dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (425.1 g) as a crude product.

後処理

  1. extractionthe mixture was extracted with hexane (2.4 L)
  2. washThe organic layer was washed with water (1.2 L) and 10 w/v % saline solution (1.2 L)
  3. extractionThe aqueous layer was extracted with hexane (2.4 L) once again
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-c72f7167c5c946c089c4f0c40f8ff930
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…