Hydrochloric Acid → HCID 69031972, compound

HRID 1867911Notes

Reaction equation

HRID 1867911 reaction equation
[N:1]([C:4]1[O:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)=[N+]=[N-].[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[O:22][CH-:21][N:20]([NH2:23])[C:19]2=O)[CH2:13][CH2:12]1.Cl.C([OH:28])C>C(O)C.O>[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[O:22][C:21](=[O:28])[N:20]([N:23]=[CH:9][C:7](=[O:8])[CH:6]=[CH:5][C:4]#[N:1])[CH2:19]2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 125701505-Azidofuran-2-carbaldehydeHCID 178514270HCID 178514270, compound

Product 1

HCID 69031972HCID 69031972, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 5-azido-2-furaldehyde (33 mg, 0.24 mmole) in 2 ml of ethanol was added dropwise to a solution of 5-morpholinomethyl-3-amino-2-oxazolidone (Sigma, 43 mg, 0.21 mmole) in 2.5 ml of ethanol:water (5:1) mixture, followed by 0.5 ml of 1N HCl. The reaction mix was stirred at room temperature overnight and evaporated to dryness. The residue was partitioned between 20 ml of ethyl acetate and 10 ml of 2% sodium bicarbonate. The ethyl acetate layer was kept and the aqueous layer extracted with 2×15 ml of ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and evaporated to dryness. (51 mg, 0.17 mmole, 83% yield). Silica gel TLC analysis showed a homogeneous single spot with Rf of 0.44 when developed in ethyl acetate. 1H NMR analysis of 4 revealed that it is a mixture of two isomers with the acrylonitrile moiety in cis (Z) and trans (E)-configurations (coupling constant J=11.6 and 16.5 Hz, respectively).

Workup

  1. additionThe reaction mix
  2. customevaporated to dryness
  3. customThe residue was partitioned between 20 ml of ethyl acetate and 10 ml of 2% sodium bicarbonate
  4. extractionthe aqueous layer extracted with 2×15 ml of ethyl acetate
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additiona mixture of two isomers with the acrylonitrile moiety in cis (Z) and trans (E)-configurations (

Sources & evidence

ORD record
ord-7ceef45c41e9474782e165a23ed21f5c
Source dataset
uspto-grants-2009_12
Patent number
US07632928B2

Reaction notes

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