Benzyl chloroformate → HCID 14326577, compound

HRID 1414022Notes

Reaction equation

HRID 1414022 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=2)[NH:6][CH:5]=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>[OH-].[Na+]>[C:21]1([CH2:20][O:19][C:17]([NH:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=3)[NH:6][CH:5]=2)=[O:18])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 19605739HCID 19605739, compound

Product 1

HCID 14326577HCID 14326577, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent3×

Procedure

A vigorously stirred solution of 3-(2-amino-ethyl)-1H-indole-5-carboxylic acid (50 g) in aqueous sodium hydroxide (1 M, 450 ml) was cooled in an icebath and benzyl chloroformate (60 ml) and aqueous sodium hydroxide (1 M, 430 ml) were added simultaneously dropwise over a period of 1 hour so as to maintain the pH >10. The reaction mixture was stirred at ca 5° C. for 1.25 hour then a further portion of aqueous sodium hydroxide (1 M, 130 ml) was added. After a further 2 hour. the reaction mixture was extracted with ether (2×500 l ml) and the aqueous layer treated with sodium chloride (200 g), acidified to pH 1 with concentrated hydrochloric acid (80 ml) and extracted with ethyl acetate (3×500 ml). The combined extracts were washed with aqueous sodium chloride (10%, 2×500 ml) dried (MgSO4) and evaporated to dryness to give the title compound as a white solid (61.8 g) mp 186.5°-188°.

Workup

  1. additionwere added simultaneously dropwise over a period of 1 hour so as
  2. temperatureto maintain the pH >10
  3. waitAfter a further 2 hour
  4. extractionthe reaction mixture was extracted with ether (2×500 l ml)
  5. additionthe aqueous layer treated with sodium chloride (200 g)
  6. extractionextracted with ethyl acetate (3×500 ml)
  7. washThe combined extracts were washed with aqueous sodium chloride (10%, 2×500 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-588153d660ac426d931d0a89eebfa8fe
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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