P,P-Diphenylphosphinic azide → HCID 58976723, compound

HRID 1179241Notes

Reaction equation

HRID 1179241 reaction equation
ClCCOC1C=C(C=C(OC)C=1OC)C(O)=O.[C:18]([O:22][C:23](=[O:39])[NH:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH2:36][CH2:37][Cl:38])[CH:26]=1)([CH3:21])([CH3:20])[CH3:19].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C(O)(C)(C)C>[C:18]([O:22][C:23](=[O:39])[NH:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH2:36][CH2:37][Cl:38])[CH:26]=1)([CH3:19])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 67274232HCID 67274232, compound

Product 1

HCID 58976723HCID 58976723, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

[3-(2-Chloro-ethoxy)-4,5-dimethoxy-phenyl]-carbamic acid tert-butyl ester 3-(2-Chloro-ethoxy)-4,5-dimethoxy-benzoic acid (500 mg, 1.9 mmol), DPPA, (550 mg, 2 mmol), and TEA, (2 mmol), were combined in 5 mL t-butanol and refluxed for 5 h. The t-butanol was removed under vacuum and the residue purified by silica gel chromatography (5% methanol/DCM, affording 90 mg [3-(2-Chloro-ethoxy)-4,5-dimethoxy-phenyl]-carbamic acid tert-butyl ester. NMR CDCl3: 6.7(d, 2H), 6.4(bs, 1H), 4.3(t, 3H), 3.85(s, 3H), 3.80(s, 3H), 3.82(m, 2H), 1.5(s, 9H).

Workup

  1. temperaturerefluxed for 5 h
  2. customThe t-butanol was removed under vacuum
  3. customthe residue purified by silica gel chromatography (5% methanol/DCM

Sources & evidence

ORD record
ord-1129aa52fa1e4976b6c3d29d57ef188a
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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