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

HRID 471300Notes

Reaction equation

HRID 471300 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:14][C:13]3([CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=4)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[CH2:16][CH2:15]3)[O:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:14][C:13]3([CH2:15][CH2:16][N:17]([CH2:20][C:21]4[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=4)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:18][CH2:19]3)[O:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57989339tert-Butyl 3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate

Product 1

HCID 579890083-(3-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate (Example 277, step a) was dissolved in DCM (10 mL) and TFA (2 mL) was added. The resulting mixture was stirred for 2 h then evaporated. The residue was azeotroped with toluene and redissolved in MeCN (10 mL). This was applied to a SCX cartridge (50 g, Varian) which had been pre-wetted with MeCN. The cartridge was washed with MeCN (100 mL) and eluted with 880 aqueous ammonia in MeCN (1:4, 100 mL). The eluent was evaporated to afford the subtitled compound. Material used directly in the next step.

Workup

  1. customthen evaporated
  2. customThe residue was azeotroped with toluene
  3. dissolutionredissolved in MeCN (10 mL)
  4. washThe cartridge was washed with MeCN (100 mL)
  5. washeluted with 880 aqueous ammonia in MeCN (1:4, 100 mL)
  6. customThe eluent was evaporated

Sources & evidence

ORD record
ord-fc0cb6ed5a2b44e2881ce3c65d8acbfa
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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