HCID 2761804, compound → HCID 59997228, compound

HRID 1815580Notes

Reaction equation

HRID 1815580 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:17]2[CH2:19][O:18]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([CH:30]([O:33][NH:34][S:35]([C:38]1[CH:46]=[CH:45][C:41]2[O:42][CH2:43][O:44][C:40]=2[CH:39]=1)(=[O:37])=[O:36])[CH2:31][CH3:32])[CH3:29]>O1CCCC1>[O:42]1[C:41]2[CH:45]=[CH:46][C:38]([S:35]([N:34]([O:33][CH:30]([CH2:31][CH3:32])[CH2:28][CH3:29])[CH2:19][C@@H:17]([OH:18])[C@@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:14][CH:13]=3)(=[O:36])=[O:37])=[CH:39][C:40]=2[O:44][CH2:43]1

Participants

4

Reactant 2

HCID 2761804HCID 2761804, compoundHCID 22500129HCID 22500129, compound

Product 1

HCID 59997228HCID 59997228, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (2.66 g, 7.2 mmol) and the N-(1-ethylpropoxy)-1,3-benzodioxole-5-sulfonamide (2.30 g, 9.0 mmol) in tetrahydrofuran (12 mL) was added phosphazene base P4 tert-butyl solution (1.44 mL, 1.44 mmol, 1M in hexane). After stirring at ambient temperature for 18 h, the reaction was concentrated in vacuo, taken up in ethyl acetate (100 mL), washed with 0.5 N hydrochloric acid (2×40 mL) followed by water (40 mL), saturated sodium bicarbonate (40 mL) and brine (40 mL), dried (magnesium sulfate) and concentrated. The residue was purified by silica gel chromatography (20% ethyl acetate in hexane) to afford the title compound (4.25 g, 90%) as a white foam. 1H NMR (DMSO-d6): δ 0.79 (6H, dt), 1.11-1.74 (4H, m), 1.17 (9H, s), 2.37 (1H, t), 2.60-3.02 (3H, m), 3.38-3.49 (1H, m), 3.50-3.61 (1H, m), 4.03 (1H, m), 5.00 (2H, s), 5.04 (1H, d), 6.15 (2H, s), 6.60 (1H, d), 7.03 (2H, d), 7.10 (1H, d), 7.17-7.38 (9H, m)

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. washwashed with 0.5 N hydrochloric acid (2×40 mL)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-eba1af43b4c742d28fbc7d0a15c43738
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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