Hydrochloric Acid → HCID 22467245, compound

HRID 381324

Reaction equation

HRID 381324 reaction equation
[F-].C([N+](CC)(CC)CC)C.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20]([C:36]3[C:44]4[C:39](=[CH:40][C:41]([CH2:45][O:46][Si](C(C)C)(C(C)C)C(C)C)=[CH:42][CH:43]=4)[N:38]([CH3:57])[CH:37]=3)[C:21]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=3[CH2:34][CH3:35])(=[O:26])=[O:25])=[O:22])=[CH:19][C:14]=2[O:13][CH2:12]1.Cl>C(#N)C>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20]([C:36]3[C:44]4[C:39](=[CH:40][C:41]([CH2:45][OH:46])=[CH:42][CH:43]=4)[N:38]([CH3:57])[CH:37]=3)[C:21]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=3[CH2:34][CH3:35])(=[O:26])=[O:25])=[O:22])=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 22467246HCID 22467246, compound

Product 1

HCID 22467245HCID 22467245, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tetraethylammonium fluoride (312 mg, 2.18 mmol) was added to a stirred solution of the compound of step (g) (380 mg, 0.55 mmol) in acetonitrile (6 ml) at room temperature under a nitrogen atmosphere. After 12 H the mixture was poured into 1M hydrochloric acid (50 ml) and extracted into ethyl acetate (2×50 ml). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo to give a yellow foam. Flash column chromatography (eluting with 98% dichloromethane/2% methanol) gave the product as a white solid (242 mg).

Workup

  1. extractionextracted into ethyl acetate (2×50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a yellow foam
  5. washFlash column chromatography (eluting with 98% dichloromethane/2% methanol)

Sources & evidence

ORD record
ord-23cd5a78594f423b8c469eb4457657cd
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Linked notes

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