Tetrahydrofuran → HCID 86608940, compound

HRID 2112416Notes

Reaction equation

HRID 2112416 reaction equation
C1[CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.C([Li])CCC.C([C:22]1[C:30]2[C:29]([NH:31][NH2:32])=[N:28][CH:27]=[N:26][C:25]=2[N:24]([C@@H:33]2[O:39][C@H:38]([CH2:40][OH:41])[C@@H:36]([OH:37])[C@@:34]2([CH3:42])[OH:35])[CH:23]=1)=O>C(Cl)(Cl)Cl.O>[NH:31]([C:29]1[C:30]2[C:22]([CH:2]=[CH:3][O:4][CH3:5])=[CH:23][N:24]([C@@H:33]3[O:39][C@H:38]([CH2:40][OH:41])[C@@H:36]([OH:37])[C@@:34]3([CH3:42])[OH:35])[C:25]=2[N:26]=[CH:27][N:28]=1)[NH2:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 86608939HCID 86608939, compoundHCID 178418339Butyllithium

Product 1

HCID 86608940HCID 86608940, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of THF at 0° C., diisopropyl ethyl amine (10 eq.), and n-butyl-lithium (10 eq.), is (Ph3P)ClCH2OCH3 (10 eq.). After stirring this mixture at room temperature for 1.5 hours, one cools to −78° C. and adds the compound from Step 2. After stirring at −78 C overnight one warms to room temperature, separates the reaction mixture between water and chloroform, extracts the aqueous layer two more times with chloroform, and combines the organic layers. They are dried over sodium sulfate, evaporated and purified via column chromatography to give the target compound.

Workup

  1. customat 0° C.
  2. stirringAfter stirring at −78 C overnight one
  3. customwarms to room temperature
  4. dry with materialThey are dried over sodium sulfate
  5. customevaporated
  6. custompurified via column chromatography
  7. customto give the target compound

Sources & evidence

ORD record
ord-96ca1fed6f774026b135f08931541985
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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