6-Chlorotryptophan → 6-Chloro-N-formyl-L-tryptophan

HRID 1658544

Reaction equation

HRID 1658544 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 227910706-Chloro-N-formyl-L-tryptophan

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-e51c20d4859a439eb115ed48f9e56aa1
Source dataset
uspto-grants-1976_06
Patent number
US03965129

Linked notes

Loading…