tert-Butanol → HCID 22627494, compound

HRID 278119Notes

Reaction equation

HRID 278119 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](C(O)=O)[CH:12]=2)[C:7]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:6]1[CH2:22][CH2:23][CH3:24].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[C:53]([OH:57])([CH3:56])([CH3:55])[CH3:54]>>[C:53]([O:57][C:51]([NH:48][C:11]1[CH:12]=[C:13]2[C:8]([C:7]([C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])=[C:6]([CH2:22][CH2:23][CH3:24])[N:5]2[CH2:4][C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]=2[Cl:1])=[CH:9][CH:10]=1)=[O:36])([CH3:56])([CH3:55])[CH3:54]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22627188HCID 22627188, compound

Product 1

HCID 22627494HCID 22627494, compound

Procedure

A mixture of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (100 mg), diphenylphosphoryl azide (97 mg) and triethylamine (53 mg) in tert-butanol (4 ml) was refluxed for 2 hours, and then partitioned between ethynyl acetate and diluted with hydrochloric acid. The organic layer was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1) to give 6-tert-butoxycarbonylamino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (125 mg) as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 2 hours
  2. custompartitioned between ethynyl acetate
  3. additiondiluted with hydrochloric acid
  4. washThe organic layer was washed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0b7a7437c51046d3beb3e7d648cdaae0
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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