Tetrahydrofuran → HCID 58697743, compound

HRID 2213374Notes

Reaction equation

HRID 2213374 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13]N3C=CN=N3)[O:10][C:9]2=[O:19])[CH:5]=[CH:4][C:3]=1[N:20]1[CH:25]=[CH:24][C:23](=[O:26])[CH2:22][CH2:21]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1C[O:40]CC1>>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:40])[O:10][C:9]2=[O:19])[CH:5]=[CH:4][C:3]=1[N:20]1[CH:25]=[CH:24][C:23](=[O:26])[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 10338372HCID 10338372, compound

Product 1

HCID 58697743HCID 58697743, compoundYield 42.8%

Procedure

A solution of the product of step 1 above (1 g, 2.9 mmol, 1 equiv) in THF anhydrous (15 mL) is cooled down to −78° C. and lithium bis(trimethylsilyl)amide 1.0 M in THF (3.2 mL, 3.2 mmol, 1.1 equiv) is added dropwise. The reaction mixture is stired at −78° C. for 1 h. (R)-(−)-Glycidal butyrate (466 mg, 0.46 mL, 3.2 mmol, 1.1 equiv) is added dropwise and the reaction mixture is allowed to gradually warm to room temperature and is left to stir over weekend. The mixture is quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (30 mL) and extracted with EtOAc (3×50 mL). The washed organics with brine are dried over (MgSO4) and concentrated. The product is purified by flash chromatography on silica gel using 1–3% MeOH in DCM as eluant to give the title compound as a solid (380 mg, 1.24 mmol, 42.8%). HPLC Rt=4.36, MS=(M+H)+=307.

Workup

  1. waitis left
  2. customThe mixture is quenched with saturated aqueous ammonium chloride (20 mL)
  3. additiondiluted with water (30 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe washed organics with brine are dried over (MgSO4)
  6. concentrationconcentrated
  7. customThe product is purified by flash chromatography on silica gel using 1–3% MeOH in DCM as eluant

Sources & evidence

ORD record
ord-de06ecd976364cb18532861bcfb531b8
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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