Lithium Hydroxide → tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate

HRID 521395ノート

反応式

HRID 521395 の反応式
[Li+].[OH-].[N+](C1C=CC(C([O:12][C@H:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([C:22]4[CH:47]=[CH:46][C:25]5[C:26]([CH:29]([C:39]6[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=6)[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[N:27][S:28][C:24]=5[CH:23]=4)[C:16]=3[C@H:15]([CH3:48])[CH2:14]2)=O)=CC=1)([O-])=O>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([CH:29]([C:26]2[C:25]3[CH:46]=[CH:47][C:22]([C:21]4[C:16]5[C@H:15]([CH3:48])[CH2:14][C@@H:13]([OH:12])[C:17]=5[N:18]=[CH:19][N:20]=4)=[CH:23][C:24]=3[S:28][N:27]=2)[CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:44][CH:43]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67437737HCID 67437737、化合物

生成物 1

HCID 67438914tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1N LiOH aqueous solution (0.30 mL, 0.30 mmol) was added to a stirred solution of (5R,7R)-4-(3-(2-(tert-butoxycarbonylamino)-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (102 mg, 0.149 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The resulting residue was purified by column chromatography (DCM:MeOH, 60:1) to give tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (62 mg, 78%) as an oil. LCMS (APCI+) m/z 537, 539 [M+H]+; Rt=3.99 min.

後処理

  1. customThe solvent was evaporated
  2. customThe resulting residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (DCM:MeOH, 60:1)

出典と根拠

ORDレコード
ord-d5c3e4db8cb84a3fb5e576d59073f00a
出典データセット
uspto-grants-2016_05
特許番号
US09328091B2

反応ノート

読み込み中…