(Diethylamino)sulfur trifluoride → HCID 58466231, compound

HRID 335964Notes

Reaction equation

HRID 335964 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:27]=1)[C:18]1[CH:17]=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:22]2(O)[CH2:25][O:24][CH2:23]2)=[CH:9][C:10]=1[F:21].C(N(S(F)(F)[F:34])CC)C>C(Cl)Cl>[F:21][C:10]1[C:11]2[O:12][C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C@@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:27]3)[C:6]=2[CH:7]=[C:8]([C:22]2([F:34])[CH2:25][O:24][CH2:23]2)[CH:9]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58466203HCID 58466203, compound

Product 1

HCID 58466231HCID 58466231, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a RBF was added (S)-3-(2-amino-5′-fluoro-2′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)oxetan-3-ol (0.28 g, 0.75 mmol, prepared as described in Method CCl4) and DCM (5 mL). The resulting mixture was then cooled to 0° C. and (diethylamino)sulfur trifluoride (0.20 mL, 1.50 mmol, Alfa Aesar) was added drop wise. The mixture was then stirred at 0° C. for 15 min and at room temperature for 15 min. Then, the mixture was quenched with saturated sodium bicarbonate (5 mL). The mixture was stirred at 0° C. for 5 min and at RT for 5 min. Then, the organic layer was collected and the aqueous layer was extracted with DCM (1×10 mL). The combined organic extracts were dried over MgSO4 and silica gel was added. The solvent was removed and the solid mixture was purified by silica gel flash column chromatography using ISCO instrument (solid loading, 20-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 375 (M+H).

Workup

  1. customThen, the mixture was quenched with saturated sodium bicarbonate (5 mL)
  2. stirringThe mixture was stirred at 0° C. for 5 min and at RT for 5 min
  3. customThen, the organic layer was collected
  4. extractionthe aqueous layer was extracted with DCM (1×10 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4 and silica gel
  6. additionwas added
  7. customThe solvent was removed
  8. customthe solid mixture was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-2710fcb7b59544aebeffd51a35171a9a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…