tert-Butanol → 3-(Octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester

HRID 1110283Notes

Reaction equation

HRID 1110283 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=1)C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])C=CC=CC=1.C([N:56]([CH2:59]C)CC)C.[Na].[C:62]([OH:66])([CH3:65])([CH3:64])[CH3:63]>>[CH3:63][C:62]([O:66][C:59](=[O:44])[NH:56][C:22]1[CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:28]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=1)([CH3:65])[CH3:64]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5360545SodiumHCID 193890463-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid

Product 1

HCID 193890303-(Octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester

Procedure

A solution of 25 g (0.05 mol) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid, 13 ml (0.06 mol) of diphenylphosphoryl azide and 8.4 ml (0.06 mol) of triethylamine in 165 ml of t-butyl alcohol (freshly distilled from sodium) was stirred at reflux under argon for 19 hours. The excess t-butyl alcohol was removed at reduced pressure and the residue was extracted with methylene chloride. The dried extract was concentrated to a solid which was purified by chromatography on 200 g of 35-70 mesh silica gel using 50% ethyl acetate-hexane to give 28 g of slightly impure 3-(octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester which was suitable for use in the next step.

Workup

  1. temperatureat reflux under argon for 19 hours
  2. customThe excess t-butyl alcohol was removed at reduced pressure
  3. extractionthe residue was extracted with methylene chloride
  4. extractionThe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas purified by chromatography on 200 g of 35-70 mesh silica gel using 50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-e3e73ae50b094e01abc01ae0486ec06c
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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