4-Nitrobenzoic Acid → HCID 86622332, compound

HRID 501700Notes

Reaction equation

HRID 501700 reaction equation
[N:1]([C@@H:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][C@H:5]1[OH:15])=[N+:2]=[N-:3].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:15][C@H:5]2[CH2:6][C:7]3[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=3)[C@H:4]2[N:1]=[N+:2]=[N-:3])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

7

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 86622333HCID 86622333, compound

Product 1

HCID 86622332HCID 86622332, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Step AC (3): To a solution of (1R,2R)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol (400 mg) from Step AC (2), 4-nitrobenzoic acid (813 mg), triphenyl phosphine (1.28 g) in benzene (10 mL) at rt was added DEAD dropwise (0.77 mL), and the reaction mixture was stirred at rt for 12 h. Saturated sodium bicarbonate was added, the aqueous layer was separated, and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo, and the residue was purified by preparative TLC eluting with 30% EtOAc/70% hexanes to give (1R,2S)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoate compound as a colorless oil (284 mg). NMR (400 MHz, CDCl3) δ 8.28 (2H, dd), 8.22 (2H, dd), 7.20 (1H, d), 6.93 (2H, m), 7.79 (1H, q), 4.94 (1H, d), 3.83 (3H, s), 3.29 (1H, dd), 3.22 (1H, dd).

Workup

  1. customthe aqueous layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by preparative TLC
  8. washeluting with 30% EtOAc/70% hexanes

Sources & evidence

ORD record
ord-7595504cc3ad448cbcfa4c82f566671c
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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