Tetrahydrofuran → HCID 67280024, compound

HRID 1694754Notes

Reaction equation

HRID 1694754 reaction equation
N(C(OCC)=O)=NC(OCC)=[O:4].[Br:13][C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[OH:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:42]1[CH2:46][O:45]C[CH2:43]1>>[Br:13][C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[O:22][C@@H:42]([CH3:43])[C:46]([OH:45])=[O:4]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 753413-Bromo-4-hydroxybenzonitrileHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 67280024HCID 67280024, compound

Procedure

Diethyl azodicarboxylate (2.12 g) was added to a stirred solution of 2-bromo-4-cyanophenol (2.0 g), methyl-R-lactate (1.47 g) and triphenylphosphine (2.65 g) in THF (80 ml). After 20 h, the mixture was filtered through silica using isohexane/EtOAc as solvent and the filtrate evaporated to dryness. The residue was dissolved in DCM (50 ml), treated with TFA (10 ml) and stirred for 2 h. The solution was evaporated and the residue partitioned between EtOAc and aqueous sodium bicarbonate. The aqueous was acidified with 2M hydrochloric acid, extracted with EtOAc, dried (MgSO4) and evaporated to give the subtitle compound.

Workup

  1. filtrationthe mixture was filtered through silica
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in DCM (50 ml)
  4. additiontreated with TFA (10 ml)
  5. customThe solution was evaporated
  6. customthe residue partitioned between EtOAc and aqueous sodium bicarbonate
  7. extractionextracted with EtOAc
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-23fac0e18c3f4baca9e2b51b7370be1e
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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