Methanol → 3-(tert-Butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid methyl ester

HRID 1527471Notes

Reaction equation

HRID 1527471 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:23][Si](C=[N+]=[N-])(C)C>C(Cl)Cl>[CH3:23][O:14][C:13](=[O:15])[C:12]1[CH:16]=[C:17]([Cl:20])[C:18]([F:19])=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 682834143-(Tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid

Product 1

HCID 682835653-(tert-Butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid (4.00 g, 13.2 mmol) in CH2Cl2 (100 mL) were added MeOH (6.94 mL, 171 mmol) and subsequently trimethylsilyldiazomethane (8.56 mL, 17.1 mmol) in a dropwise manner over 15 min. Stirring was continued at RT for 4.5 h. Volatiles were then evaporated under reduced pressure to afford the title compound as a colorless oil, which was used directly in the next step without further purification. TLC Rf (c-hexane/EtOAc 6:1)=0.40; tR (HPLC conditions c): 5.56 min.

Workup

  1. customVolatiles were then evaporated under reduced pressure

Sources & evidence

ORD record
ord-e050be8953534939ab3e3edcec890caa
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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