Water → HCID 66750565, compound

HRID 643872Notes

Reaction equation

HRID 643872 reaction equation
[CH2:1]([O:8][C:9]1[C:10](C(O)=O)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:32]([CH2:35]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])=CC=1.O.[CH3:55][C:56]([OH:59])([CH3:58])[CH3:57]>C1(C)C=CC=CC=1>[C:56]([O:59][C:35](=[O:44])[NH:32][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][C:17]2[C:12](=[CH:13][C:14]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:16]=2)[CH:11]=1)([CH3:58])([CH3:57])[CH3:55]

Participants

7

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66750570HCID 66750570, compound

Product 1

HCID 66750565HCID 66750565, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3,7-bis-benzyloxynaphthalene-2-carboxylic acid (0.768 g, 2 mmol) in anhydrous t-BuOH (8 mL) and anhydrous toluene (8 mL) is added triethylamine (0.303 g, 3 mmol). To the resulting solution is added DPPA (0.715 g, 2.6 mmol) and the mixture is stirred at room temperature for 5 min, then stirred at 100° C. for 18 h. The mixture is allowed to cool to room temperature and then poured into water. The mixture is extracted into EtOAc and the organic phase is washed with saturated NaCl. The solvent is removed-under reduced pressure and the resulting residue is purified by flash chromatography, eluting with DCM to afford (3,7-bis-benzyloxynaphthalene-2-yl)-carbamic acid tert-butyl ester as a white solid: mp=179-182° C.

Workup

  1. stirringstirred at 100° C. for 18 h
  2. temperatureto cool to room temperature
  3. extractionThe mixture is extracted into EtOAc
  4. washthe organic phase is washed with saturated NaCl
  5. customthe resulting residue is purified by flash chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-46e27b3429ca47bcb78c327811328efe
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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