Trifluoroacetic acid → HCID 45100909, compound

HRID 1096289Notes

Reaction equation

HRID 1096289 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C@@H:17]([CH3:47])[C:18]([N:20]([CH2:41][CH:42](OC)OC)[CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:32][CH2:31][C:28]3([CH2:30][CH2:29]3)[C@H:27]([O:33][Si](CC)(CC)CC)[CH2:26]2)=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15].C([SiH](CC)CC)C.C(N(CC)CC)C>>[Cl:8][C:9]1[CH:10]=[C:11]([N:16]2[CH2:42][CH2:41][N:20]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:32][CH2:31][C:28]4([CH2:29][CH2:30]4)[C@H:27]([OH:33])[CH2:26]3)[C:18](=[O:19])[C@@H:17]2[CH3:47])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 12052TriethylsilaneHCID 66783284HCID 66783284, compound

Product 1

HCID 45100909HCID 45100909, compoundYield 52%

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (255 mg, 2.24 mmol) was added at RT to a solution of (S)-2-(3,4-dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-[4-((S)-4-triethylsilanyloxy-6-aza-spiro[2.5]oct-6-yl)-butyl]-propionamide (92 mg, 0.15 mmol), then after 30 min triethylsilane (87 mg, 0.75 mmol) was added. The reaction mixture was stirred for 16 h, then cooled to 0° C. and treated with triethylamine (226 mg, 2.24 mmol). The ice bath was removed, then after 15 min the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2→CH2Cl2/MeOH/25% aq. ammonia solution 80:20:1) afforded the title compound (34 mg, 52%). Light yellow gum, MS: 440.3 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. customafter 15 min the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-07d77cfaeb194e798197211dbb4f2ded
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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