Triethylamine → HCID 86633533, compound

HRID 1693228Notes

Reaction equation

HRID 1693228 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 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 86633534HCID 86633534, compound

Product 1

HCID 86633533HCID 86633533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl(±)-[(4aR*,6R*,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 64-(4) (500 mg) was dissolved in THF. Then, perfluorobutanesulfonyl fluoride (0.43 mL, specific gravity: 1.682 g/cm3), a triethylamine-trihydrofluoric acid complex (0.39 mL, specific gravity: 0.989 g/cm3) and triethylamine (0.99 mL, specific gravity: 0.73 g/cm3) were sequentially added at room temperature. After completion of the addition, the mixture was stirred for 15 hours. The reaction solution was concentrated under reduced pressure and then the residue was purified by silica gel column chromatography to obtain the title compound (351 mg).

Workup

  1. additionAfter completion of the addition
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-915ca83c85424a07b606f3024871faf6
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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