3-Nitrophenol → HCID 54544611, compound

HRID 2259206Notes

Reaction equation

HRID 2259206 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCC[C@H]1C(O)=O)(OC(C)(C)C)=O.[N+:29]([C:32]1[CH:33]=[C:34](O)[CH:35]=[CH:36][CH:37]=1)([O-:31])=[O:30].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([N+:29]([O-:31])=[O:30])[CH:37]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 5462977Diethyl azodicarboxylateHCID 11074142(R)-1-Boc-2-azetidinemethanol

Product 1

HCID 54544611HCID 54544611, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.25 g (1.2 mmol) sample of (R)-1-t-butoxycarbonyl-2-azetidinemethanol (prepared as in Example 1b above, except replacing the N-BOC-L-proline thereof with N-BOC-S-azetidinecarboxylic acid) and 2.25 g (18 mmol) of 3-nitrophenol (Aldrich) were added to a complex of TPP and DEAD (prepared as in Example 1 above, 18.1 mmol of each)in 80 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was chromatographed on silica gel, eluting with a gradient of 1:1, 1:2, 1:3, 1:4 chloroform:hexane to give 1.5 g (40%) of the title compound.

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was chromatographed on silica gel
  3. washeluting with a gradient of 1:1, 1:2, 1:3, 1:4 chloroform

Sources & evidence

ORD record
ord-7cc66e7bf0754abf983f53914c16fc72
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

Loading…