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2,6-Di-tert-butyl-4-methylpyridine → tert-Butyl {[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate

HRID 222160
ノート
印刷プレビュー

反応式

HRID 222160 の反応式
[C@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@H:20]4[CH2:24][C@H:23]([OH:25])[C@H:22]([CH2:26][OH:27])[CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.Cl[S:44]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])(=[O:46])=[O:45]>C(C#N)(C)=O>[C:50]([O:49][C:48](=[O:54])[NH:47][S:44]([O:27][CH2:26][C@@H:22]1[CH2:21][C@@H:20]([N:17]2[C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][C@H:1]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:3][CH2:2]4)[C:12]=3[CH:19]=[CH:18]2)[CH2:24][C@@H:23]1[OH:25])(=[O:46])=[O:45])([CH3:53])([CH3:51])[CH3:52]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 66618256(1S,2S,4R)-4-{-4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol

生成物 1

HCID 86614247tert-Butyl {[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate収率 37%

試薬・触媒・溶媒 1

HCID 694302-Oxopropiononitrile溶媒

実験手順

(1S,2S,4R)-4-{4-[(1R)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentanol (27.6 mg, 0.117 mmol) and 2,6-di-tert-butyl-4-methylpyridine (48.5 mg, 0.236 mmol) were suspended in AcCN (1.57 mL) and cooled to 0° C. tert-Butyl (chlorosulfonyl)carbamate was added and the mixture was allowed to warm to rt overnight. The reaction was quenched via addition of MeOH (1.00 mL) and concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (15.2 mg, 37%). LC/MS: Rt=1.29 min, ES+ 544 (FA standard).

後処理

  1. additionwas added
  2. customThe reaction was quenched via addition of MeOH (1.00 mL)
  3. concentrationconcentrated in vacuo
  4. washSilica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM

出典と根拠

ORDレコード
ord-7c7a89e2fe3245ad9219ba3e7889c57a
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

読み込み中…

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