Triethylamine → HCID 59621340, compound

HRID 1693227Notes

Reaction equation

HRID 1693227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:17][CH2:16][C@H:15](O)[CH2:14][C@H:13]1[CH2:12][S:11][C:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:9]2.[F:27]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C(N(CC)CC)C>C1COCC1>[F:27][C@@H:15]1[CH2:16][CH2:17][C@:8]2([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:9]=[C:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:11][CH2:12][C@@H:13]2[CH2:14]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 67814Perfluoro-1-butanesulfonyl fluoride2×HCID 59621330HCID 59621330, compound

Product 1

HCID 59621340HCID 59621340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl(±)-[(4aR*,6S*,8aS*)-8a-(2-fluorophenyl)-6-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate obtained in Preparation Example 63-(4) (1.5 g) was dissolved in THF. Then, perfluorobutanesulfonyl fluoride (1.36 mL, specific gravity: 1.682 g/cm3), a triethylamine-trihydrofluoric acid complex (1.23 mL, specific gravity: 0.989 g/cm3) and triethylamine (3.15 mL, specific gravity: 0.73 g/cm3) were sequentially added at room temperature. After completion of the addition, the mixture was stirred for 16 hours. The mixture was heated to 50° C. and further stirred for 24 hours. Perfluorobutanesulfonyl fluoride (0.68 mL), a triethylamine-trihydrofluoric acid complex (0.62 mL) and triethylamine (1.58 mL) were further sequentially added to the mixture, followed by further stirring with heating under reflux for eight hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography to obtain the title compound (106 mg).

Workup

  1. additionAfter completion of the addition
  2. stirringfurther stirred for 24 hours
  3. stirringby further stirring
  4. temperaturewith heating
  5. temperatureunder reflux for eight hours
  6. temperatureThe reaction solution was cooled to room temperature
  7. concentrationconcentrated under reduced pressure
  8. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ab54c53a45a457990932fecb3e6a432
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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