Methanol → (3-Carbamoyl-6-methoxy-indol-1-yl)-acetic acid

HRID 1527209Notes

Reaction equation

HRID 1527209 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([C:19](=[O:21])[NH2:20])=[CH:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[C:19]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:8]([CH2:7][C:6]([OH:22])=[O:5])[CH:9]=1)(=[O:21])[NH2:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 68283635(3-Carbamoyl-6-methoxy-indol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 68283427(3-Carbamoyl-6-methoxy-indol-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-carbamoyl-6-methoxy-indol-1-yl)-acetic acid tert-butyl ester (300 mg, 0.99 mmol) in CH2Cl2 (9 mL) was added TFA (4.5 mL) at RT, and stirring was continued for 2 h. Methanol was then added to the reaction mixture, and volatiles were removed in vacuo. The residue was taken up in methanol and concentrated under reduced pressure to afford the title compound as a grey solid: MS: 249 [M+H]+, 497 [2M+H]+; tR (HPLC conditions c): 2.86 min. The material thus obtained was used in the next reaction step without further purification.

Workup

  1. customwere removed in vacuo
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed6f8aec7bea42ac9490230756d657bb
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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