Sodium Bicarbonate → HCID 44377804、化合物

HRID 1061256ノート

反応式

HRID 1061256 の反応式
[BH4-].[Na+].[N:3]([CH2:6][C@@H:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:20])=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:14]=1)[OH:8])=[N+]=[N-].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:55]=[CH:54][C:45]([CH2:46][CH:47]3[S:51][C:50](=[O:52])[NH:49][C:48]3=[O:53])=[CH:44][CH:43]=2)[CH2:38][CH2:37]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C(O)(=O)C>[Cl:20][C:12]1[CH:11]=[CH:10][C:9]([C@@H:7]([OH:8])[CH2:6][NH:3][CH:36]2[CH2:41][CH2:40][N:39]([C:42]3[CH:55]=[CH:54][C:45]([CH2:46][CH:47]4[S:51][C:50](=[O:52])[NH:49][C:48]4=[O:53])=[CH:44][CH:43]=3)[CH2:38][CH2:37]2)=[CH:14][C:13]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

参加物

9

反応物 5

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydride2 回HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 86584545HCID 86584545、化合物

生成物 1

HCID 44377804HCID 44377804、化合物

試薬・触媒・溶媒 3

HCID 24463Copper sulfate pentahydrate触媒HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of copper(ll) sulfate pentahydrate (0.042 g, 0.17 mmol) in N,N-dimethylformamide (15 mL) was added sodium borohydride (0.037 g, 1 mmol). To the resulting suspension was added N-[5-((1R)-2-azido-1-hydroxy-ethyl)-2-chloro-phenyl]-methanesulfonamide (which was obtained in Example 25) (0.11 g, 0.38 mmol). After stirring for 20 minutes more copper(II) sulfate pentahydrate (0.042 g, 0.17 mmol) and sodium triacetoxyborohydride (0.064 g, 0.3 mmol) was added. The reaction mixture was stirred for 2.5 hours and then 5-[4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) (0.116 mg, 0.38 mmol), sodium triacetoxyborohydride (0.212 g, 1.0 mmol), and acetic acid (0.2 mL) were added. After stirring for 1.5 hours aqueous sodium bicarbonate solution was added and the resulting solid was collected. The product was purified by flash silica gel chromatography eluting with methylene chloride and methanol to give the title compound as a pale grey solid; mp >105° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.30-1.50 (m, 2H), 1.80-2.00 (m, 2H), 2.60-3.60 (m, 9H), 3.00 (s, 3H), 4.40-4.55 (m, 1H), 4.65-4.75 (m, 1H), 6.84 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.4 Hz, 1H), 7.20 (d, J=8.1 Hz, 1H), 7.40-7.50 (m, 2H); MS (ES) m/z: 553.2 (MH+, 100%); HRMS Calcd. for C24H30ClN4O5S2 (MH+): 553.1440. Found: 553.1336.

後処理

  1. additionwas added
  2. additionwas added
  3. customthe resulting solid was collected
  4. customThe product was purified by flash silica gel chromatography
  5. washeluting with methylene chloride and methanol

出典と根拠

ORDレコード
ord-aee41d14bd8d43b9af531b3a806a4def
出典データセット
uspto-grants-2003_02
特許番号
US06525202B2

反応ノート

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