HCID 69938093, compound → HCID 69937546, compound

HRID 2281846Notes

Reaction equation

HRID 2281846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]12[CH2:19][O:18][CH2:17][C@H:16]1[C:15](=[O:20])[N:14]([CH3:21])[C:13]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:12]2>[Zn]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]23[CH2:19][O:18][CH2:17][C@H:16]2[C:15](=[O:20])[N:14]([CH3:21])[C:13]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[N:12]3)[CH:4]=1

Participants

3

Reactant 1

HCID 69938093HCID 69938093, compound

Product 1

HCID 69937546HCID 69937546, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
0 °C

Procedure

(±)-tert-Butyl ((4aS*,7aS*)-7a-(2-fluoro-5-nitrophenyl)-3-methyl-4-oxo-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (60 mg, 0.14 mmol) was transferred into the reaction vessel. Zinc (100 mg, 1.53 mmol) was transferred into the reaction vessel. The reaction was stirred at 0° C. for 30 mins. The reaction was filtered, concentrated and the residue was purified by flash chromatography (EtOAc/Hexane, 20-100%) to give the title compound (56 mg). LCMS (Method A) Rt 2.33 min, ESI-MS: m/z 279 [MH-BOC]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography (EtOAc/Hexane, 20-100%)

Sources & evidence

ORD record
ord-283d9ca2a1324c19b3c6be84f29d8534
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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