Tetrahydrofuran → HCID 68602437, compound

HRID 1783433Notes

Reaction equation

HRID 1783433 reaction equation
[C:1]([O:5][C:6]([N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:9]1[CH:14]=[C:13]([CH2:15][C@H:16]2[C:19](=[O:20])[NH:18][C@@H:17]2[C:21]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[O:22])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:41]1COCC1.[Si](C=[N+]=[N-])(C)(C)C.C(OCC)(=O)C>CO>[C:1]([O:5][C:6]([N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:9]1[CH:14]=[C:13]([CH2:15][C@H:16]2[C:19](=[O:20])[NH:18][C@@H:17]2[C:21]([N:23]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH3:41])=[O:22])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 68600714HCID 68600714, compound

Product 1

HCID 68602437HCID 68602437, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 98 (18 mg, 1.0 eq.) in MeOH: THF (1 mL: 300 uL) was added 2.0M TMSCHN2 in hexanes (266 uL, 17 eq.). After 15 minutes, TLC showed complete conversion of starting material. The reaction was poured into ethyl acetate and then washed with 0.2N HCl, 1N NaHCO3 and brine. The organic layer was then dried over sodium sulfate and concentrated in vacuo. The product was then purified via reverse phase HPLC (C18, acetonitrile/water with 0.1% TFA) to yield 99 (11.9 mg, 65%) as a clear oil.

Workup

  1. washwashed with 0.2N HCl, 1N NaHCO3 and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe product was then purified via reverse phase HPLC (C18, acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-9fb793bea16643dfa66d04e0341185a6
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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