ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide

HRID 849730
ノート
印刷プレビュー

反応式

HRID 849730 の反応式
[CH3:1][CH:2]([CH3:13])[CH2:3][CH:4]([CH2:8][S:9][C:10](=[O:12])[CH3:11])[C:5]([OH:7])=O.[O:14]=[C:15]1[CH2:32][CH2:31][C:30]2=[CH:33][N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=32)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1.CC[N:36]=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[C:10]([S:9][CH2:8][CH:4]([CH2:3][CH:2]([CH3:1])[CH3:13])[C:5]([NH:36][C@H:32]1[CH2:31][C:30]2=[CH:33][N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=32)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:15]1=[O:14])=[O:7])(=[O:12])[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acidHCID 700960479-Oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraene

生成物 1

HCID 86752869(10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide収率 85%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-methyl-2-acetylthiomethylpentanoic acid (612 mg, 3 mmol), (10S)-10-amino-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraene (427 mg, 1.5 mmol), and HOBtH2O (230 mg, 1.5 mmol) in dry DMF (30 mL) under argon at room temperature was added EDCI (863 mg, 4.5 mmol) in one portion. After stirring overnight, DMF was removed at 30° C. under high vacuum to give a yellowish semi-solid. It was dissolved in ethyl acetate (50 mL), washed with 1N HCl (30 mL), 5% NaHCO3 solution (30 mL) and finally brine (30 mL). The organic layer was dried (MgSO4) and evaporated to dryness. The resulting pale yellow-oil was stirred in 50% ether-pet. ether (40 mL) to yield 600 mg (85%) of (10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide as 1:1 stereoisomeric mixture. The stereoisomeric mixture was separated in flash column chromatography (LPS-2), eluted with 20% ethyl acetate in pet. ether to give the less polar stereoisomer, m.p. 226° C., and the more polar stereoisomer, m.p. 220° C.

後処理

  1. customDMF was removed at 30° C. under high vacuum
  2. customto give a yellowish semi-solid
  3. washwashed with 1N HCl (30 mL), 5% NaHCO3 solution (30 mL) and finally brine (30 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to dryness
  6. stirringThe resulting pale yellow-oil was stirred in 50% ether-pet. ether (40 mL)

出典と根拠

ORDレコード
ord-9d2effa9f6c547cca0aa6fa4ed295f68
出典データセット
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06013792

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート