Hydrochloric Acid → HCID 86681636, compound

HRID 571220Notes

Reaction equation

HRID 571220 reaction equation
C(OC([NH:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:10]=1)=O)(C)(C)C.[ClH:24].O1CCOCC1>C(Cl)Cl>[ClH:24].[NH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866816351H-Indole-1-acetic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl ester

Product 1

HCID 86681636HCID 86681636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(3-(tert-butoxycarbonylamino)-1H-indol-1-yl)acetate (275 mg, 0.864 mmol) in dry DCM (8 ml), cooled at 0° C. and under nitrogen, 4N HCl in dioxane (2.159 ml, 8.64 mmol) was added, and the mixture was stirred at room temperature for 36 hours. The solvent was removed under reduced pressure without heating to give ethyl 2-(3-amino-1H-indol-1-yl)acetate hydrochloride (220 mg, 0.864 mmol, quantitative yield). MS/ESI+ 219.1 [MH]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. temperaturewithout heating

Sources & evidence

ORD record
ord-0ea932c3a3514d3f8ebba6a52bf77971
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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