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Sulfuric acid magnesium salt (1:1) → tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710374
Notes
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Reaction equation

HRID 710374 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][N:22]4[CH2:27][C:28]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30][CH2:29]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2]>ClCCCl.C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[CH2:27][C:28]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:42])[CH3:41])[CH2:29][O:30][C:31]([CH3:34])([CH3:35])[O:32][CH2:33]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66726782tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86661784tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 28.6%

Reagents, catalysts & solvents 3

HCID 14801
Manganese dioxide
Catalyst
HCID 111,2-DichloroethaneSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of the product of Example 34, Step D (0.07 g; 0.118 mmol), MnO2 (0.58 g; 6.67 mmol) and anhydrous MgSO4 (0.5 g; 4.2 mmol) in 1,2-dichloroethane (2.5 ml) was vigorously stirred for 2 h at ˜50° C., then overnight at room temperature. This was diluted to 20 ml with CH2Cl2 and filtered through Celite pad, washed with fresh CH2Cl2 (10 ml). The combined organic phase was evaporated under reduced pressure and the residue was purified by FCC (SiO2, CH2Cl2/EtOAc 9:1) to give the title compound (0.02 g; 28%), as creamy solid. 1H-NMR (CDCl3) 1.43-1.53 (m, 21H+H2O); 3.78 (d, 2H, J=11.9 Hz); 3.90 (d, 2H, J=11.9 Hz); 4.13-4.38 (m, 5H); 4.76 (s, 1H); 6.98 (d, 1H, J=8.5 Hz); 7.15 (s, 1H); 7.28-7.34 (m, 2H); 7.68 (d, 1H, J=8.4 Hz); 7.73 (d, 1H, J=1.9 Hz); 7.83 (dd, 1H, J=1.9, 8.4 Hz); 8.03 (d, 1H, J=7.2 Hz).

Workup

  1. customovernight
  2. customat room temperature
  3. filtrationfiltered through Celite pad
  4. washwashed with fresh CH2Cl2 (10 ml)
  5. customThe combined organic phase was evaporated under reduced pressure
  6. customthe residue was purified by FCC (SiO2, CH2Cl2/EtOAc 9:1)

Sources & evidence

ORD record
ord-78edccd3b57e440fb27da0e16c1c3902
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181182B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes