6-Chlorotryptophan → N-formyl-6-chlorotryptophan

HRID 1288448Notes

Reaction equation

HRID 1288448 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]2[NH:8][CH:9]=[C:10]([CH2:11][CH:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:3]=2[CH:2]=1.[CH:17](OC(=O)C)=[O:18]>>[CH:17]([NH:16][C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][C:10]1[C:3]2[C:4](=[CH:5][C:6]([Cl:7])=[CH:1][CH:2]=2)[NH:8][CH:9]=1)=[O:18]

Participants

3

Reactant 2

HCID 652596-ChlorotryptophanHCID 75269Acetic-formic anhydride

Product 1

HCID 22791070N-formyl-6-chlorotryptophan

Procedure

15 g(628 mM) of dl-6-chlorotryptophan was treated with 15 ml of acetic-formic anhydride. An exothermic reaction ensued, accompanied by solidification of the reaction slurry. Excess solvents were distilled off under vacuum and the resultant solids, after first leaching with dilute acid, were recrystallized from ethyl acetate to yield 12.45 g, 74%, of product, m.p. 181°-3° dec.

Workup

  1. customAn exothermic reaction
  2. distillationExcess solvents were distilled off under vacuum
  3. additionthe resultant solids, after first leaching with dilute acid
  4. customwere recrystallized from ethyl acetate
  5. customto yield 12.45 g, 74%

Sources & evidence

ORD record
ord-ee27346fa3ca4db9a4bb3595ed96824f
Source dataset
uspto-grants-1976_10
Patent number
US03988349

Reaction notes

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