Ammonia → HCID 20298252, compound

HRID 1389127Notes

Reaction equation

HRID 1389127 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH3:7].[CH:8]1([CH2:11][C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)[CH2:10][CH2:9]1.Cl>C(OCC)C>[CH:8]1([CH2:11][C:12]2[NH:13][C:14]([CH:3]([C:2]([OH:6])=[O:5])[NH2:7])=[CH:15][CH:16]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 15620607Glyoxylic acid, monohydrateHCID 20298260HCID 20298260, compound

Product 1

HCID 20298252HCID 20298252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Glyoxylic acid hydrate (8.3 g., 0.09 mole) was dissolved in 0.880 sp. gr. ammonia solution (50 ml.) and the solution heated to 50°-60°. 2-Cyclopropylmethyl pyrrole (10.9 g., 0.09 mole) was added dropwise and the resulting mixture stirred at 50°-60° for 2 hours. Diethyl ether (50 ml.) was added to the cool reaction mixture. Filtration gave a solid which was washed with diethyl ether (50 ml.). The filtrate was shaken and the aqueous phase separated and combined with the filtered solid to give a slurry whose pH was adjusted to ca. 5 with concentrated hydrochloric acid. The mixture was filtered and the resulting solid thoroughly washed with water, acetone, and with diethyl ether, affording, after drying in vacuo, DL-2-(5-cyclopropylmethyl-2-pyrrolyl)glycine (9.65 g., 55%), M.P. 203°-205° (decomp.).

Workup

  1. filtrationFiltration
  2. customgave a solid which
  3. washwas washed with diethyl ether (50 ml.)
  4. stirringThe filtrate was shaken
  5. customthe aqueous phase separated
  6. customto give a slurry whose pH
  7. filtrationThe mixture was filtered
  8. washthe resulting solid thoroughly washed with water, acetone
  9. customwith diethyl ether, affording
  10. dry with materialafter drying in vacuo, DL-2-(5-cyclopropylmethyl-2-pyrrolyl)glycine (9.65 g., 55%), M.P. 203°-205° (decomp.)

Sources & evidence

ORD record
ord-3cbff6c0cc5c43058983be31d64e7430
Source dataset
uspto-grants-1981_01
Patent number
US04243672

Reaction notes

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