Toluene → HCID 68680868, compound

HRID 645357Notes

Reaction equation

HRID 645357 reaction equation
[C:1]([O:4][CH:5]([C:47]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=1)[CH2:6][CH2:7][C@H:8]1[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:15][CH:14]=2)[C@@H:9]1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]2([O:43][C:44](=[O:46])[CH3:45])[CH2:40][O:39]C(C)(C)[O:37][CH2:36]2)=[CH:29][CH:28]=1)(=[O:3])[CH3:2].[C:54](O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C1COCC1.O>[C:44]([O:43][C:35]([CH2:40][OH:39])([CH2:36][OH:37])[CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([C@@H:9]2[C@@H:8]([CH2:7][CH2:6][C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C:47]3[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=3)[C:11](=[O:12])[N:10]2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH2:26][CH3:54])(=[O:24])=[O:25])=[CH:15][CH:14]=2)=[CH:28][CH:29]=1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 68618773HCID 68618773, compound

Product 1

HCID 68680868HCID 68680868, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of the intermediate of step E (1.5 g, 2 mmol) in THF/water (16 mL/4 mL) was added TFA (1 mL). The reaction mixture was stirred at RT for 16 hr. To the reaction mixture was added 100 mL toluene and the water was removed under vacuum with water bath temperature of 40° C. The residue was treated twice with 100 mL toluene followed by azeotropic removal of water. The solvent was completely removed under vacuum. The crude product was purified by MPLC (silica column) with stepwise gradient elution (50-100% EtOAc/hexanes as eluent). Mixed fractions were also isolated and were further purified by prep TLC eluting with CH2Cl2/MeOH (95/5). The purified fractions were combined to afford the title compound. m/z (ES) 653 (M-OAc)+.

Workup

  1. customthe water was removed under vacuum with water bath temperature of 40° C
  2. additionThe residue was treated twice with 100 mL toluene
  3. customfollowed by azeotropic removal of water
  4. customThe solvent was completely removed under vacuum
  5. customThe crude product was purified by MPLC (silica column) with stepwise gradient elution (50-100% EtOAc/hexanes as eluent)
  6. customMixed fractions were also isolated
  7. customwere further purified by prep TLC
  8. washeluting with CH2Cl2/MeOH (95/5)

Sources & evidence

ORD record
ord-647321f58c6a4c74a3da39a8bcfa7c38
Source dataset
uspto-grants-2010_04
Patent number
US07704988B2

Reaction notes

Loading…