Tetrahydrofuran → HCID 59302561, compound

HRID 2237439Notes

Reaction equation

HRID 2237439 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:20][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2].[CH2:22]1COCC1.C(N(C(C)C)CC)(C)C.[Si](C=[N+]=[N-])(C)(C)C>CO>[CH2:1]([O:3][C:4]([C:6]1[S:20][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[O:21][CH3:22])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 59302577HCID 59302577, compound

Product 1

HCID 59302561HCID 59302561, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step b) (2.3 g, 7.3 mmol) was dissolved in 60 mL of 1:1 MeOH:THF. Diisopropylethylamine (1.9 mL, 10.9 mmol) was added followed by TMSCHN2 (10.9 mL of 2M). The reaction was stirred overnight at room temperature then quenched carefully with 0.4 ML HOAc. After stirring ½ hour, the reaction was partitioned between DCM and 1M HCl (100 mL each). The organic layer was dried over MgSO4 and concentrated to give 2.75 g of the subtitle compound.

Workup

  1. customthen quenched carefully with 0.4 ML HOAc
  2. stirringAfter stirring ½ hour
  3. customthe reaction was partitioned between DCM and 1M HCl (100 mL each)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e78726f873354b85a7031bb7822372d3
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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