HCID 86693883, compound → HCID 71664659, compound

HRID 1504990Notes

Reaction equation

HRID 1504990 reaction equation
C([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C@@H:16]2[C:26]3([CH2:28][CH2:27]3)[C@H:25]3[C@@H:18]([O:19][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:23][CH2:24]3)[C@@H:17]2[F:41])[C:10]1=[O:42])(=O)C1C=CC=CC=1>CO.N.C(O)(C(F)(F)F)=O.O>[F:41][C@H:17]1[C@H:18]([OH:19])[C@@H:25]([CH2:24][OH:23])[C:26]2([CH2:27][CH2:28]2)[C@H:16]1[N:11]1[CH:12]=[CH:13][C:14](=[O:15])[NH:9][C:10]1=[O:42]

Participants

5

Reactant 1

HCID 86693883HCID 86693883, compound

Product 1

HCID 71664659HCID 71664659, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

Compound 28 (0.2 g, 0.32 mmol) was dissolved in saturated MeOH with NH3 (20 mL) and stirred for 8 h at room temperature. The solvent was evaporated under vacuum and the residue was purified by silica gel vacuum column (35% EtOAc/hexane) to give the debenzolated compound. Debenzoylated compound was dissolved in 10 mL of CF3COOH/H2O (2:1, v/v) and heated to 50° C. for 3 h. The solvent was removed under vacuum and the residue was co-evaporated with ethanol (3×10 mL) under vacuum. The residue was purified by combiflash chromatography (7% MeOH/CH2Cl2) to give 29 in 60 mg (68%) as white foam. [α]24D 5.4° (c 0.67, MeOH); 1H NMR (500 MHz, DMSO-d6) δ 11.17 (bs, 1H), 7.68 (d, J=15.6, 1 H), 5.80 (d, J=19.7, 1H), 5.67 (d, J=14.5 Hz, 1H), 4.74-4.78 (bs, 2H, —OH), 4.70 (m, 1H), 4.10-4.13 (bm, 1H, —OH), 3.32-3.43 (m, 2H), 2.1-2.08 (m, 1H), 0.69-0.74 (m, 1H), 0.49-0.56 (m, 2H), 0.43 (m, 1H); 13C NMR (500 MHz, MeOH-d4) δ 164.9, 161.4, 152.3, 140.2, 109.6, 76.0, 74.0, 60.2, 51.4, 21.1, 14.7, 11.0, 7.3; HR-MS Cald. For (C12H15FN2O4+H)+ 270.16. found 270.1226.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was purified by silica gel vacuum column (35% EtOAc/hexane)
  3. customto give the debenzolated compound
  4. temperaturev/v) and heated to 50° C. for 3 h
  5. customThe solvent was removed under vacuum
  6. customThe residue was purified by combiflash chromatography (7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-38c57e1dfc454441a08815791d2f79b4
Source dataset
uspto-grants-2015_12
Patent number
US09216960B2

Reaction notes

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