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Diisopropylethylamine → tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate

HRID 2389334
ノート
印刷プレビュー

反応式

HRID 2389334 の反応式
Cl.[NH2:2][C@@H:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].[C:10]([O:14][C:15]([N:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:26](O)=[O:27])[C:20]=2[CH:19]=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.O>[OH:9][CH2:8][C@H:3]([NH:2][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[CH:18][N:17]2[C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])=[O:27])[C:4]([O:6][CH3:7])=[O:5]
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 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 497588501-Boc-4-carboxyindole

生成物 1

HCID 68536502tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate収率 72.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (1.25 g), 1-(tert-butoxycarbonyl)-1H-indole-4-carboxylic acid (2.10 g) and N-ethyl-N-isopropyl-2-propanamine (2.94 mL) in DMF (25.0 mL) was added dropwise DPPA (1.91 mL) at 0° C. and the mixture was stirred at ambient temperature for 3 days. The resulting mixture was diluted with water (50.0 mL) and extracted with EtOAc (75 mL). The organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution. and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=99:1) to afford tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate (2.12 g) as a colorless syrup.

後処理

  1. extractionextracted with EtOAc (75 mL)
  2. washThe organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution
  3. dry with materialand brine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=99:1)

出典と根拠

ORDレコード
ord-34eb15dc93cc451596386ad354cc21ed
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273745B2

反応ノート

読み込み中…

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