Hydrochloric Acid → HCID 22093486, compound

HRID 457993Notes

Reaction equation

HRID 457993 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:13]=3[N:14]=2)=[O:7])=[C:4]([OH:24])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].Cl>CC(C)=O.C(OCC)(=O)C>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][O:24][C:4]1[CH:3]=[C:2]([F:1])[CH:23]=[CH:22][C:5]=1[C:6](=[O:7])[NH:8][CH2:9][C:10]1[S:11][C:12]2[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:13]=2[N:14]=1)[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18468188HCID 18468188, compound

Product 1

HCID 22093486HCID 22093486, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 4-fluoro-2-hydroxy-N-(4,5,7,-trifluoro-benzothiazol-2-ylmethyl)-benzamide (1.0 g, 2.8 mmol) in acetone (14 mL) was treated with aq 2 N K2CO3 (2.1 mL, 4.2 mmol) and ethyl bromoacetate (2 mL, 19 mmol) and heated to 45° C. for 5 h. After cooling to room temperature, the solution was acidified to a pH 1 with aq 2 N HCl. The resulting solution was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated. Purification by MPLC (10–100% ethyl acetate in heptane 23 mL/min, 75 min) provided {5-fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid ethyl ester (1.0 g, 81%) as a white crystalline solid: 1H NMR (DMSO-d6 300 MHz) δ 9.32 (t, J=5.9 Hz, 1 H), 7.94 (dd, J1=9.0 Hz, J2=7.2 Hz, 1 H), 7.80–7.70 (m, 1 H), 7.13 (dd, J1=11.1 Hz, J2=2.4 Hz, 1 H), 6.95 (dt, J1=8.4 Hz, J2=2.5 Hz, 1 H), 5.02 (s, 2 H), 4.94 (d, J=6 Hz, 2 H), 4.17 (q, J=7.2 Hz, 2 H), 1.18 (t, J=7.1 Hz, 3 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated NaCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by MPLC (10–100% ethyl acetate in heptane 23 mL/min, 75 min)

Sources & evidence

ORD record
ord-ee8d1ea04e0f45b895f2ec1cc212cef8
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

Loading…