Trifluoroacetic acid → HCID 90067498, compound

HRID 929167Notes

Reaction equation

HRID 929167 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:19]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[C:20]4[C:21]([N:48]=3)=[N:22][C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][CH:35]5[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]5)=[CH:29][CH:28]=3)=[C:24]([Cl:26])[CH:25]=4)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:19]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:54])([CH3:55])[CH3:56])[C:20]4[C:21]([N:48]=3)=[N:22][C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][CH:35]5[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]5)=[CH:29][CH:28]=3)=[C:24]([Cl:26])[CH:25]=4)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 89558611HCID 89558611, compound

Product 1

HCID 90067498HCID 90067498, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-((4-(2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)phenyl)ethynyl)piperidine-1-carboxylate (147 mg, 0.178 mmol) in anhydrous DCM (2.0 mL) at room temperature was added trifluoroacetic acid (0.2 mL). The reaction was stirred for 2 h at room temperature, and then poured into saturated aqueous sodium bicarbonate (40 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate, and then concentrated under reduced pressure to afford the title compound as a colorless oil. LC-MS: calculated for C37H53ClN4O5Si2 724.32 observed m/e: 725.32 (M+H)+ (Rt 2.56/4 min).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f028798d8a944da8b2dc3238e2cf7208
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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