tert-Butanol → HCID 22627494, compound

HRID 1108735Notes

Reaction equation

HRID 1108735 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 ethyl 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 ethyl 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-f838ee11f1aa417abfff1495b7019ccb
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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