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Disodium 2,3-dihydroxybutanedioate → (S)-tert-Butyl 1-oxo-1-(2-(tetrahydro-2H-pyran-4-yl carbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525036
ノート
印刷プレビュー

反応式

HRID 525036 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH3:29])[C:17]([NH:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](OC)=[O:26])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:18]=[C:17]([NH:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](=[O:26])[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C@@H:16]([NH:15][C:13](=[O:14])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:29]
参加物反応条件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 13355Disodium 2,3-dihydroxybutanedioateHCID 4192234-AminotetrahydropyranHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

生成物 1

HCID 86722055(S)-tert-Butyl 1-oxo-1-(2-(tetrahydro-2H-pyran-4-yl carbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

Tetrahydro-2H-pyran-4-amine (900 microl, 8.69 mmols) was added to a solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.89 mmols, preparation 109) in toluene (36 ml). A 2M solution of Trimethyl aluminium in toluene (7 ml, 14.00 mmols) was added and it was stirred at 80° C. overnight. Water (50 ml) and a 0.5M solution of sodium tartrate (25 ml) were added. It was extracted with ethylacetate. The combined organic layers were washed with water and brine. It was dried, filtered and concentrated in vacuum. The title compound was obtained (617 mg, 56%).

後処理

  1. extractionIt was extracted with ethylacetate
  2. washThe combined organic layers were washed with water and brine
  3. customIt was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-04de8d8e819c4455b3734c36e5918338
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340547B2

反応ノート

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