Sodium Bicarbonate → HCID 44377804, compound

HRID 1061256Notes

Reaction equation

HRID 1061256 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

HCID 44377804HCID 44377804, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aee41d14bd8d43b9af531b3a806a4def
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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