Trifluoroacetic acid water → HCID 69828668, compound

HRID 1839246Notes

Reaction equation

HRID 1839246 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([C@@H:10]2[C@@H:14]3[O:15]C(C)(C)[O:17][C@H:13]3[C@H:12]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][CH:23]=[N:24][C:25]=4[NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])[O:11]2)[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O>C(=O)(O)[O-].[Na+]>[C:1]([C:5]1[N:9]=[C:8]([C@@H:10]2[C@@H:14]([OH:15])[C@@H:13]([OH:17])[C@H:12]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][CH:23]=[N:24][C:25]=4[NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])[O:11]2)[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 69827510HCID 69827510, compound

Product 1

HCID 69828668HCID 69828668, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 9-{(3aR,4R,6S,6aR)-6-[3-(tert-butyl)-1,2,4-oxadiazol-5-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-N-isobutyl-9H-purin-6-amine (14 mg) in a cold mixture of trifluoroacetic acid:water (9:1; 1 ml) was kept at 4° C. for 18 h. The resulting solution was basified in an ice bath with saturated aqueous sodium bicarbonate (20 ml), extracted with ethyl acetate (2×20 ml), the extracts dried (MgSO4) and evaporated to dryness in vacuo to afford the title compound (7.66 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. dry with materialthe extracts dried (MgSO4)
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-746de1cefda1484585fb620cb7b79433
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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