(Diethylamino)sulfur trifluoride → HCID 69084882, compound

HRID 1396251Notes

Reaction equation

HRID 1396251 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([C@H:12](O)[CH3:13])[C@@H:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C@H:8]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:6]2[N:7]=1.CCN(S(F)(F)[F:42])CC>ClCCl>[F:42][C@H:12]([C@H:10]1[O:11][C@H:5]2[C@H:6]([N:7]=[C:3]([N:2]([CH3:35])[CH3:1])[S:4]2)[C@@H:8]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C@@H:9]1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH3:13]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 69083695HCID 69083695, compound

Product 1

HCID 69084882HCID 69084882, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-1-((3aR,5R,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanol (280 mg, 0.56 mmol) in dichloromethane (10 mL) was treated with DAST (900 mg, 5.59 mmol) at −78° C. for 10 min and at 0° C. for 1 hr. The reaction was quenched by sat. aqueous Na2CO3 solution (30 mL), and extracted with dichloromethane (2×20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue, which was purified by silica gel column, eluted with 1-2% methanol in dichloromethane to give compound 50 as a yellow syrup (240 mg, 85%). (ES, m/z): [M+H]+ 505.0; 1H NMR (300 MHz, CDCl3) δ 7.22-7.43 (m, 4H), 6.83-6.94 (m, 4H), 6.38-6.50 (m, 1H), 4.58-4.78 (m, 6H), 3.75-3.90 (m, 8H), 3.46-3.50 (m, 1H), 3.05-3.18 (m, 6H), 1.27-1.36 (m, 3H).

Workup

  1. customThe reaction was quenched by sat. aqueous Na2CO3 solution (30 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide a residue, which
  6. customwas purified by silica gel column
  7. washeluted with 1-2% methanol in dichloromethane

Sources & evidence

ORD record
ord-ae7b48ef1d304609975dc7f965e381c7
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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