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Lithium aluminum hydride → N-[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]-N-methylsulfamide

HRID 222209
ノート
印刷プレビュー

反応式

HRID 222209 の反応式
C(O[C:6](=O)[N:7]([S:41]([NH2:44])(=[O:43])=[O:42])[CH2:8][C@@H:9]1[CH2:13][C@@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@@H:10]1[O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])(C)(C)C.[AlH4-].[Li+]>O1CCCC1>[Si:34]([O:33][C@H:10]1[CH2:11][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:13][C@H:9]1[CH2:8][N:7]([CH3:6])[S:41]([NH2:44])(=[O:42])=[O:43])([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:35])[CH3:36]
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

4

反応物 2

HCID 28112Lithium aluminum hydrideHCID 58944590tert-butyl (aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate

生成物 1

HCID 58944658N-[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]-N-methylsulfamide

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

tert-Butyl(aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)-methyl]carbamate (108 mg, 0.000164 mol) was dissolved in tetrahydrofuran (2.0 mL) under an atmosphere of nitrogen. Lithium tetrahydroaluminate (12.5 mg, 0.000329 mol) was added and the mixture heated at 50° C. for 80 minutes. The reaction was then cooled, quenched with water and acidified to ˜pH 6 with 1M HCl. This mixture was then extracted with ethyl acetate, the separated organic phase was evaporated, and the residue was purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product, 25 mg (27%). LC/MS: Rt=2.34 min, ES+ 571 (AA standard).

後処理

  1. temperatureThe reaction was then cooled
  2. customquenched with water
  3. extractionThis mixture was then extracted with ethyl acetate
  4. customthe separated organic phase was evaporated
  5. customthe residue was purified by silica gel chromatography
  6. washeluting with 10 to 100% ethyl acetate in hexanes
  7. customto yield the product, 25 mg (27%)

出典と根拠

ORDレコード
ord-79fed75d5d624056ba91a5ec4713f0ce
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207177B2

反応ノート

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