Trifluoroacetic acid → HCID 46214970, compound

HRID 237290Notes

Reaction equation

HRID 237290 reaction equation
C(OC([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH3:12])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:14]([CH:19]=1)[O:13][C:10]1([CH3:12])[CH2:11][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67347111HCID 67347111, compound

Product 1

HCID 46214970HCID 46214970, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-bromo-2-phenethyloxy-phenoxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (20 mg) and TFA (1 mL) in CH2Cl2 (2 mL) was stirred at rt for 2 h. The reaction was concentrated in vacuo and purified by PTLC followed by additional purification using RP HPLC (Agilent) to give the title compound as an oil (12 mg, 77%). MS (ESI): mass calcd. for C18H20BrNO2, 362.3; m/z found, 362.0 [M+H]+. 1H NMR (CDCl3): 7.38-7.18 (m, 5H), 7.04 (dd, J=8.6, 2.3 Hz, 1H), 6.74 (dd, J=5.5, 3.1, 2H), 4.15 (t, J=7.2 Hz, 2H), 3.97 (d, J=8.9 Hz, 2H), 3.45 (d, J=9.2 Hz, 2H), 3.11 (t, J=7.1 Hz, 2H), 1.98 (s, 1H), 1.65 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by PTLC
  3. customfollowed by additional purification

Sources & evidence

ORD record
ord-7ad06f25c47a4b0b92960934e130eb17
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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