4-Nitrobenzoic Acid → HCID 118101240, compound

HRID 708897Notes

Reaction equation

HRID 708897 reaction equation
[F:1][C:2]1[C:3]([O:24][C@H:25]2[C@H:29]([OH:30])[CH2:28][O:27][CH2:26]2)=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1)([O-:33])=[O:32].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:31]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([O:30][C@@H:29]2[C@H:25]([O:24][C:3]3[C:2]([F:1])=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:4]=3[CH2:5][N:6]([C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH3:17])[CH2:26][O:27][CH2:28]2)=[O:39])=[CH:41][CH:42]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 118092995HCID 118092995, compound

Product 1

HCID 118101240HCID 118101240, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 27C (250 mg, 0.595 mmol) was mixed with 4-nitrobenzoic acid (447 mg, 2.68 mmol), PPh3 (741 mg, 2.82 mmol) in THF (1.5 mL) and stirred at rt for 10 min. The reaction was cooled to 0° C., then DIAD (0.589 mL, 2.97 mmol) was added. After stirring at rt for 16 h, the reaction was quenched with H2O and extracted with EtOAc (2×). The organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography to give 27D (268 mg, 0.471 mmol, 79% yield) as a white foam. The relative stereochemistry of hydroxyether is cis however absolute stereochemistry is undetermined MS (ESI) m/z: 570.4 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringAfter stirring at rt for 16 h
  3. customthe reaction was quenched with H2O
  4. extractionextracted with EtOAc (2×)
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2bfecdd9818641c797a11e9dfa48b1d2
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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