Trifluoroacetic acid → HCID 86629212, compound

HRID 2384935Notes

Reaction equation

HRID 2384935 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[O:22][CH3:23])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C@@H:10]2[CH2:9][NH:8][CH2:12][C@H:11]2[OH:13])=[C:16]([O:22][CH3:23])[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68960634HCID 68960634, compound

Product 1

HCID 86629212HCID 86629212, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(4-bromo-2-methoxy-phenoxy)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (603 mg, 1.55 mmol) in dichloromethane (10 mL) and cool the mixture to 0° C. Add trifluoroacetic acid (2.0 mL, 26.45 mmol) and warm the mixture to room temperature for one hour. Remove the volatiles via reduced pressure and then apply to two 10 g SCX cartridges. Wash the material with methanol then elute the material with 2N ammonia in methanol to give 420 mg (93%) of the title compound as a clear oil. LC-MS/ES m/z (81Br) 290.0 [M+H]+.

Workup

  1. customRemove the volatiles via reduced pressure
  2. washWash the material with methanol
  3. washthen elute the material with 2N ammonia in methanol

Sources & evidence

ORD record
ord-9fcdb711a420427999e088ffe0ed84e0
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

Loading…