Tetrahydrofuran → HCID 178451914, compound

HRID 1470948Notes

Reaction equation

HRID 1470948 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:25]2[CH:30]=[CH:29][C:28]([C:31]3[N:32]=[C:33]([C@@H:36]4[CH2:40][CH2:39][CH2:38][N:37]4[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[NH:34][CH:35]=3)=[CH:27][CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[H][H]>C(O)C.[Pt](=O)=O>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH:15]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:6][CH:7]=3)[CH:12]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[N:32]=[C:33]([C@@H:36]5[CH2:40][CH2:39][CH2:38][N:37]5[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[NH:34][CH:35]=4)=[CH:27][CH:26]=3)[CH2:13][CH2:14]2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 178418361HCID 178418361, compoundHCID 178451916HCID 178451916, compound

Product 1

HCID 178451914HCID 178451914, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The product from example 40C (1.37 g, 2.153 mmol), in ethanol (10 mL) and THF (10 mL) then added platinum(IV) oxide (196 mg, 0.862 mmol) and a hydrogen balloon and stirred the solution at room temperature for 48 h. The reaction was then treated according to the procedure in Example 39G to provide the title compound (1.3 g, 100%) as a mixture of stereoisomers.

Workup

  1. additionThe reaction was then treated

Sources & evidence

ORD record
ord-36478e75704c4e3fbadcbf8e0286eebc
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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