Acetic Anhydride → HCID 68411356, compound

HRID 705247Notes

Reaction equation

HRID 705247 reaction equation
[OH:1][CH:2]1[CH:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][CH:3]1[CH3:25].[CH3:26][C:27](OC(C)=O)=[O:28]>N1C=CC=CC=1>[C:27]([O:1][CH:2]1[CH:3]([CH3:25])[CH2:4][C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:6][CH:7]1[NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15])(=[O:28])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67135398Tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

Product 1

HCID 68411356HCID 68411356, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (+/−)-tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in pyridine (0.1 M) was added Ac2O (2.0 equiv.) and the reaction was stirred at room temperature overnight. Upon completion, the reaction was concentrated to dryness, then worked-up with ethyl acetate and water. The organic phase was dried with brine, then sodium sulfate, filtered, and concentrated to give (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl acetate in 94% yield. LC/MS=392.2 (M+H), Rt=0.94 min.

Workup

  1. concentrationUpon completion, the reaction was concentrated to dryness
  2. dry with materialThe organic phase was dried with brine
  3. filtrationsodium sulfate, filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8f07ed2d7fe475298ec2d45ee23ed4d
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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