tert-Butanol → HCID 86617227, compound

HRID 1675733Notes

Reaction equation

HRID 1675733 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15](C(O)=O)[CH:16]=3)[CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[CH3:46][C:47]([OH:50])([CH3:49])[CH3:48]>>[O:1]=[C:2]1[C:10]2([CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:41][C:44](=[O:29])[O:50][C:47]([CH3:49])([CH3:48])[CH3:46])[CH:16]=3)[CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59166732HCID 59166732, compound

Product 1

HCID 86617227HCID 86617227, compound

Procedure

A solution of (±)-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-indole]-5-carboxylic acid from Step B (65.0 mg, 0.233 mmol), diphenylphosphoryl azide (0.060 mL, 0.279 mmol), and triethylamine (0.039 mL, 0.279 mmol) in t-BuOH (5 mL) was heated to reflux for 3 h. The reaction mixture was concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 50:50, to give the title compound. MS: m/z=295 (M-C4H7).

Workup

  1. temperatureto reflux for 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-c483a1f1cf5d4809bb0510317a169ab6
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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