Trifluoroacetic acid → HCID 69111953, compound

HRID 900261Notes

Reaction equation

HRID 900261 reaction equation
C([O:5][C:6]([C:8]1[N:9]([CH2:22][C:23]2[CH:27]=[C:26]([C:28]3[S:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[O:25][N:24]=2)[C:10]([C:13]([N:15]2[CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])=[N:11][CH:12]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:33][C:30]1[S:29][C:28]([C:26]2[O:25][N:24]=[C:23]([CH2:22][N:9]3[C:8]([C:6]([OH:7])=[O:5])=[CH:12][N:11]=[C:10]3[C:13]([N:15]3[CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])[CH:27]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69112333HCID 69112333, compound

Product 1

HCID 69111953HCID 69111953, compound

Conditions

Temperature
40 °C

Procedure

To the resulting solution containing 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-([1,4]oxazepane-4-carbonyl)-3H-imidazole-4-carboxylic acid tert-butyl ester was added TFA (216 μL). The mixture was stirred for 3 h at RT and for 3 h at 40° C. More TFA (1 mL) was added and stirring was continued at 50° C. for 2 h. The mixture was concentrated under reduced pressure. The residue was evaporated three times from toluene to provide crude 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-([1,4]oxazepane-4-carbonyl)-3H-imidazole-4-carboxylic acid (311 mg) which was directly used in the next step.

Workup

  1. stirringstirring
  2. waitwas continued at 50° C. for 2 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customThe residue was evaporated three times from toluene

Sources & evidence

ORD record
ord-359e9311a10e4667848d9a2a734a3d8c
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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