Glycine → HCID 19829962, compound

HRID 1493615Notes

Reaction equation

HRID 1493615 reaction equation
[NH2:1]CC(O)=O.[CH2:6]([C:8]1[CH:9]=[C:10]([NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][CH:13]=1)[CH3:7].N([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH3:19][O:18][C:16](=[O:17])[CH2:15][N:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:6][CH3:7])[CH:9]=1)[NH2:1]

Participants

7

Reactant 3

HCID 750GlycineHCID 23668193Sodium NitriteHCID 28584403HCID 28584403, compound

Product 1

HCID 19829962HCID 19829962, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To the glycine (Intermediate 38; 35 g; 0.181 mol) in acetic acid (50 ml) at -5° C. was added, dropwise, a solution of sodium nitrite (13.75 g; 0.199 mol) in H2O (10 ml). The temperature of the reaction mixture was not allowed to rise above 0°. After stirring for a further 2 h, zinc dust (26.02 g, 0.398 mol) was added portionwise, once again so as not to allow the temperature of the reaction mixture to rise above 0°. After 5 h, a further quantity of zinc dust (13.01 g, 0.199 mol) was added and the mixture was stirred overnight. The excess zinc dust was removed by filtration through celite. The reaction mixture was then quenched with sodium bicarbonate solution. Extraction into ethyl acetate followed by washing with water, brine and finally drying (over Na2SO4) gave the crude title compound (ca. 35 g). This crude material was chromatographed using Ethyl acetate: Petroleum ether (1:3) to yield Intermediate 39 (5.21 g; 14%) as an oil.

Workup

  1. customto rise above 0°
  2. customto rise above 0°
  3. waitAfter 5 h
  4. stirringthe mixture was stirred overnight
  5. customThe excess zinc dust was removed by filtration through celite
  6. customThe reaction mixture was then quenched with sodium bicarbonate solution
  7. extractionExtraction into ethyl acetate
  8. washby washing with water, brine
  9. dry with materialfinally drying (over Na2SO4)
  10. customgave the crude title compound (ca. 35 g)
  11. customThis crude material was chromatographed

Sources & evidence

ORD record
ord-402fbc3b6ef54cc0b08149aa7d39c3bf
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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