4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester → 4-([3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid

HRID 2303521Notes

Reaction equation

HRID 2303521 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH2:27][CH3:28])=[C:14]2[C:29](=[O:33])[C:30]([NH2:32])=[O:31])(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:32][C:30](=[O:31])[C:29]([C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][C:6]([OH:34])=[O:5])[CH:12]=2)[N:16]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]=1[CH2:27][CH3:28])=[O:33]

Participants

4

Reactant 1

HCID 108139834-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester

Product 1

HCID 99312854-([3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acidYield 63.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 450 mg (0.97 mmol) of 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester in 75 mL of methylene chloride and 1 mL of trifluoroacetic acid was stirred at room temperature for 2.25 hours and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with EtOAc to give 250 mg (63% yield) of 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid, mp 173-175° C.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was chromatographed on silica gel
  3. washeluted with EtOAc

Sources & evidence

ORD record
ord-e116df229b0f4d33b3b8a5062fb7faf0
Source dataset
uspto-grants-2002_08
Patent number
US06433001B1

Reaction notes

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