Triethylamine → (S)-((3R,3aR,6R,6aR)-6-((4-nitrophenoxy)carbonyloxy)hexahydrofuro[3,2-b]furan-3-yl)5,6-bis(nitrooxy)hexanoate

HRID 1643409Notes

Reaction equation

HRID 1643409 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9]([O:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C@H:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:16][O:17][N+:18]([O-:20])=[O:19])[C@H:5]2[O:4][CH2:3]1.CCN(CC)CC.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1)=[O:35]>C1COCC1>[N+:43]([C:40]1[CH:41]=[CH:42][C:37]([O:36][C:34]([O:1][C@H:2]2[C@H:6]3[O:7][CH2:8][C@@H:9]([O:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C@H:15]([O:21][N+:22]([O-:24])=[O:23])[CH2:16][O:17][N+:18]([O-:20])=[O:19])[C@H:5]3[O:4][CH2:3]2)=[O:35])=[CH:38][CH:39]=1)([O-:45])=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58209439(S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate

Product 1

HCID 59178148(S)-((3R,3aR,6R,6aR)-6-((4-nitrophenoxy)carbonyloxy)hexahydrofuro[3,2-b]furan-3-yl)5,6-bis(nitrooxy)hexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)5,6bis(nitrooxy)hexanoate (0.80 g, 2.18 mmol) and Et3N (0.66 g, 6.54 mmol) in THF (30 mL) was added 4-Nitrophenyl chloroformate (0.44 g, 2.18 mmol) as solid. After stirring at rt over night, the mixture was concentrated. The residue was diluted with EtOAc and washed with NaH2PO4 5%. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1; column SNAP 50; TLC method: n-hexane/ethyl acetate 1/1; Rf=0.38), affording the title product as a pale yellow oil. 1H-NMR (300 MHz, CDCl3); δ 8.32-8.29 (2H, m), 7.44-7.28 (2H, m), 5.33 (1H, m), 5.21-5.05 (2H, m), 4.89-4.65 (3H, m), 4.50 (1H, m), 4.20-3.95 (4H, m), 3.94-3.85 (1H, m), 2.50 (2H, m), 1.84 (4H, m).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with NaH2PO4 5%
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Biotage SP1; column SNAP 50; TLC method: n-hexane/ethyl acetate 1/1; Rf=0.38)

Sources & evidence

ORD record
ord-d18a60ad7ca842649e91152fde36ca9e
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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