Tert-butyl 2-[4-[4-(trifluoromethylsulfonyl)anilino]cyclohexoxy]acetate → 2-[4-[4-(Trifluoromethylsulfonyl) anilino]cyclohexoxy]acetic acid

HRID 1772291Notes

Reaction equation

HRID 1772291 reaction equation
[F:1][C:2]([F:29])([F:28])[S:3]([C:6]1[CH:27]=[CH:26][C:9]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]>FC(F)(F)C(O)=O>[F:28][C:2]([F:1])([F:29])[S:3]([C:6]1[CH:27]=[CH:26][C:9]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

3

Reactant 1

HCID 86719526Tert-butyl 2-[4-[4-(trifluoromethylsulfonyl)anilino]cyclohexoxy]acetate

Product 1

HCID 867195272-[4-[4-(Trifluoromethylsulfonyl) anilino]cyclohexoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 2-[4-[4-(trifluoromethylsulfonyl) anilino]cyclohexoxy]acetate (0.7 g, 1.6 mmol, 1 eq.) in trifluoroacetic acid (3 mL) was stirred at room temperature for 2 hours. The mixture was concentrated under vacuum to remove excess trifluoroacetic acid. The crude material was dried under high vacuum overnight to obtain 2-[4-[4-(trifluoromethylsulfonyl) anilino]cyclohexoxy]acetic acid as light brown syrup. (0.79 g, 100%); (CI, m/z): [M+H]+ 382; 1H NMR (400 MHz, CD3OD): δ 7.65 (d, J=9.0 Hz, 2H), 6.76 (d, J=9.2 Hz, 2H), 4.13 (s, 2H), 3.37-3.51 (m, 2H), 2.03-2.20 (m, 4H), 1.26-1.54 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto remove excess trifluoroacetic acid
  3. dry with materialThe crude material was dried under high vacuum overnight

Sources & evidence

ORD record
ord-ebe8ee1cd528492db44449f20a8b8b3c
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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