Acetic Acid → (1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 222168ノート

反応式

HRID 222168 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[C@@:36](C)([OH:37])[C@@H:23]5[O:24]C(C6C=CC(OC)=CC=6)[O:26][CH2:27][C@@H:22]5[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.N[C@@H]1C2C(=CC=CC=2)CC1.O.CC(O)=O>C1COCC1>[C@@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@@H:20]4[CH2:21][C@@H:22]([CH2:27][OH:26])[C@@H:23]([OH:24])[C@H:36]4[OH:37])[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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 70000841-Aminoindane, (S)-HCID 66618631(4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-ol

生成物 1

HCID 66618091(1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-ol (312 mg, 0.594 mmol, as prepared following the procedure in Example 1a-d, using (S)-(+)-1-aminoindan in step c) in THF (1.17 mL) and water (1.17 mL) was added AcOH (3.51 mL, 61.7 mmol) under an atmosphere of nitrogen. The mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound as a white solid (182 mg, 76%). LC/MS: Rt=0.85 min, ES+ 381 (FA standard).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM

出典と根拠

ORDレコード
ord-2ae5f79e0a084b2888bc16d1c21d0be2
出典データセット
uspto-grants-2012_06
特許番号
US08207177B2

反応ノート

読み込み中…