Triphenylphosphine → HCID 86585638, compound

HRID 2119614Notes

Reaction equation

HRID 2119614 reaction equation
[F:1][C:2]1[C:3]([F:41])=[CH:4][C:5]2[C:10]3[C:11]4[C:38](=[O:39])[NH:37][C:36](=[O:40])[C:12]=4[C:13]4[C:14]5[C:19]([N:20]([C@@H:22]6[O:29][C@H:28]([CH2:30][OH:31])[C:27]([F:33])([F:32])[C@H:25](O)[C@H:23]6[OH:24])[C:21]=4[C:9]=3[NH:8][C:6]=2[CH:7]=1)=[CH:18][C:17]([F:34])=[C:16]([F:35])[CH:15]=5.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[C:3]([F:41])=[CH:4][C:5]2[C:10]3[C:11]4[C:38](=[O:39])[NH:37][C:36](=[O:40])[C:12]=4[C:13]4[C:14]5[C:19]([N:20]([C@@H:22]6[O:29][C@@H:28]7[CH2:30][O:31][C@@H:25]([C:27]7([F:33])[F:32])[C@H:23]6[OH:24])[C:21]=4[C:9]=3[NH:8][C:6]=2[CH:7]=1)=[CH:18][C:17]([F:34])=[C:16]([F:35])[CH:15]=5

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86585639HCID 86585639, compound

Product 1

HCID 86585638HCID 86585638, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3,9,10-tetrafluoro-12-(4-deoxy-4,4-difluoro-β-D-glucopyranosyl)-6,7,12,13-tetrahydro(5H)indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione (0.035 g, 0.060 mmol) in 4 mL of dry THF was added triphenylphosphine (0.048 g, 0.18 mmol) and DIAD (0.035 mL, 0.18 mmol), at room temperature under Ar. The resulting reddish-orange solution was stirred at room temperature for 18 h and then it was partitioned with ethyl acetate-water. The organic phase was separated, washed (brine), dried (Na2SO4) and evaporated to give a yellow gum. This residue was purified by prep. tlc (20×20 cm×0.5 mm SiO2/THF-hexane, 1:1) and the major fraction was repurified by prep. hplc to give the title compound (0.009 g, 29%) as a yellow solid: 1H NMR (acetone-d6, 400 MHz) δ 10.67 (s, 1H), 9.83 (s, 1H), 8.88 (m, 1H), 8.73 (m, 1H), 7.56 (m, 2H), 6.44 (m, 1H), 4.91 (m, 2H), 4.47 (d, J=10.0 Hz, 1H), 4.41(d, J=11.0 Hz, 1H), 4.27 (m, 1H); MS (ESI−) m/e 560 (M−H)−; HPLC: 91.1% (320 nm).

Workup

  1. customat room temperature
  2. customit was partitioned with ethyl acetate-water
  3. customThe organic phase was separated
  4. washwashed (brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give a yellow gum
  8. customThis residue was purified by prep
  9. customtlc (20×20 cm×0.5 mm SiO2/THF-hexane, 1:1) and the major fraction was repurified by prep

Sources & evidence

ORD record
ord-e82f96207a6d44339a0cfe314beae271
Source dataset
uspto-grants-2004_02
Patent number
US06686385B2

Reaction notes

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