Isopropanol → HCID 86708076, compound

HRID 1524371Notes

Reaction equation

HRID 1524371 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:47])([F:46])[CH2:26][C@@H:27]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[NH:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)(=[O:31])=[O:30])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[CH3:48][CH:49](O)[CH3:50].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:47])([F:46])[CH2:26][C@@H:27]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[N:28]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)(=[O:30])=[O:31])[CH:49]([CH3:50])[CH3:48])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 3776Isopropanol2×HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 68044637HCID 68044637, compound

Product 1

HCID 86708076HCID 86708076, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the material from Step 9 (150 mg, 0.222 mmol), 2-propanol (0.034 mL, 0.443 mmol) and Ph3P (116 mg, 0.443 mmol) in THF (1 mL) at 0° C. was slowly added diisopropyl azodicarboxylate (0.086 mL, 0.443 mmol). The reaction mixture was stirred at room temperature overnight. LCMS showed about 50% conversion, more 2-propanol (0.034 mL, 0.443 mmol), Ph3P (116 mg, 0.443 mmol) and diisopropyl azodicarboxylate (0.086 mL, 0.443 mmol) were added, stirred for 8 hours, LCMS showed no progress. It was concentrated to dryness and the residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) to afford 81 mg of the title compound as a colorless foam. LCMS (M+1)=719.

Workup

  1. customat 0° C.
  2. additionwere added
  3. stirringstirred for 8 hours
  4. concentrationIt was concentrated to dryness
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fd36a99b9434e31a775c632d0e004a2
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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