Trifluoroacetic acid → HCID 59159305, compound

HRID 1096284Notes

Reaction equation

HRID 1096284 reaction equation
FC(F)(F)C(O)=O.C([Si](C)(C)[O:13][C@@H:14]1[CH2:21][N:20]([CH2:22][CH2:23][CH2:24][N:25]([CH2:38][CH:39](OC)OC)[C:26](=[O:37])[CH2:27][NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH2:19][CH2:18][C:15]21[CH2:17][CH2:16]2)(C)(C)C.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:36][C:31]1[CH:30]=[C:29]([N:28]2[CH2:39][CH2:38][N:25]([CH2:24][CH2:23][CH2:22][N:20]3[CH2:19][CH2:18][C:15]4([CH2:17][CH2:16]4)[C@H:14]([OH:13])[CH2:21]3)[C:26](=[O:37])[CH2:27]2)[CH:34]=[CH:33][C:32]=1[Cl:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66783154HCID 66783154, compound

Product 1

HCID 59159305HCID 59159305, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Trifluoroacetic acid (1.51 g, 13.3 mmol) was added to a solution of N-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-2-(3,4-dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-acetamide (142 mg, 0.24 mmol) in CH2Cl2 (1 mL) at RT, then after 3 h triethylsilane (140 mg, 1.21 mmol) was added. The solution was heated at 60° C. over 72 h, then partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc/MeOH 19:1) afforded the title compound (17 mg, 17%). Yellow gum, MS: 412.2 (M+H)+.

Workup

  1. custompartitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-515711de486c4be8bc5edbe071c3df53
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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