Methanol → HCID 68284195, compound

HRID 1527224Notes

Reaction equation

HRID 1527224 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][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][CH:14]=[C:13]([O:17][CH3:18])[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 68283765HCID 68283765, compound

Product 1

HCID 68284195HCID 68284195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-carbamoyl-5-methoxy-indol-1-yl)-acetic acid tert-butyl ester (45.0 mg, 0.118 mmol) in CH2Cl2 (2.0 mL) was added TFA (1.0 mL) at RT, and stirring was continued for 3 h. Methanol was then added to the reaction mixture and volatiles were removed in vacuo. The residue was taken up in methanol and concentrated again under reduced pressure to afford the title compound as a beige solid: MS (LC/MS): 249 [M+H]+, 277 [M+Na]+; tR (HPLC conditions c): 2.93 min. The material thus obtained was used in the next reaction step without further purification.

Workup

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

Sources & evidence

ORD record
ord-7c045e72f2274afd989a5063e23dc43b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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