Trifluoroacetic acid → 3-(2-Chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid

HRID 1255317Notes

Reaction equation

HRID 1255317 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:26]([CH2:27][N:28]2[CH2:47][CH2:46][C:31]3([O:36][CH2:35][CH2:34][N:33]([C:37]([C:39]4[N:40]=[C:41]([CH2:44][CH3:45])[S:42][CH:43]=4)=[O:38])[CH2:32]3)[CH2:30][CH2:29]2)=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17]>C(Cl)Cl>[Cl:8][C:9]1[C:26]([CH2:27][N:28]2[CH2:29][CH2:30][C:31]3([O:36][CH2:35][CH2:34][N:33]([C:37]([C:39]4[N:40]=[C:41]([CH2:44][CH3:45])[S:42][CH:43]=4)=[O:38])[CH2:32]3)[CH2:46][CH2:47]2)=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58168518Tert-butyl 3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate

Product 1

HCID 581684923-(2-Chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to a solution of tert-butyl 3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate [Example 26, step d] (3.1 g) in DCM (30 mL) and the resulting mixture stirred for 2 h, then evaporated. The residue was partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (50 mL). The phases were separated and the aqueous phase was washed with more ethyl acetate (2×100 mL). The aqueous phase was then acidified with acetic acid and extracted with ethyl acetate (3×100 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a white foam. Yield 2.7 g.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (50 mL)
  3. customThe phases were separated
  4. washthe aqueous phase was washed with more ethyl acetate (2×100 mL)
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic solutions were dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-bd7fac5f93c749ac908caddcac857caa
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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