Triethylamine → HCID 69280858, compound

HRID 1425673Notes

Reaction equation

HRID 1425673 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.C(O[CH:10]1[C@H:15]([N:16]=[C:17]=[S:18])[C@@H:14]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]([O:23][C:24](=[O:26])[CH3:25])[C@@H:12]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:11]1)(=O)C.C(N(CC)CC)C>ClCCl>[C:24]([O:23][C@@H:13]1[C@@H:12]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:11][C@H:10]2[C@H:15]([N:16]=[C:17]([N:2]3[CH2:5][CH2:4][CH2:3]3)[S:18]2)[C@H:14]1[O:19][C:20](=[O:22])[CH3:21])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12308726Azetidine hydrochlorideHCID 86707003HCID 86707003, compound

Product 1

HCID 69280858HCID 69280858, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of azetidine hydrochloride (12 g, 129 mmol) and (3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (48 g, 123 mmol) in dichloromethane (500 mL) was treated with triethylamine (18.7 g, 185 mmol) for 1 h at room temperature, and followed by addition oftrifluoroacetic acid (56.2 g, 493 mmol). The reaction mixture was stirred overnight at room temperature, and then quenched by aqueous sodium bicarbonate. The organic layer was separated, dried over anhydrous MgSO4, and condensed under vacuum to give a residue, which was purified by a silica gel column, eluted with 1% methanol in dichloromethane to provide compound 2 as a light yellow syrup (29 g, 61%). (ES, m/z) [M+H]+ 386.9; 1H NMR (300 MHz, CDCl3) 6.28-6.30 (d, J=6.6 Hz, 1H), 5.44-5.46 (m, 1H), 4.95-4.99 (m, 1H), 4.34-4.37 (t, J=5.4 Hz, 1H), 4.04-4.17 (m, 6H), 3.86-3.92 (m, 1H), 2.34-2.44 (m, 2H), 2.06-2.14 (m, 9H).

Workup

  1. customquenched by aqueous sodium bicarbonate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous MgSO4, and condensed under vacuum
  4. customto give a residue, which
  5. customwas purified by a silica gel column
  6. washeluted with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-902dfc9654e04dbcb4a8850586278e2d
Source dataset
uspto-grants-2015_01
Patent number
US08933040B2

Reaction notes

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