Sodium Hydroxide → 1-(4-Azidobutanoyl)-4-(1,3-dihydroxypropan-2-yloxy)-7-nitroindoline

HRID 16574Notes

Reaction equation

HRID 16574 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]([N:9]1[C:17]2[C:12](=[C:13]([O:21][CH:22]([CH2:28][O:29]C(=O)C)[CH2:23][O:24]C(=O)C)[CH:14]=[CH:15][C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)=[O:8])=[N+:2]=[N-:3].[OH-].[Na+]>CO.O>[N:1]([CH2:4][CH2:5][CH2:6][C:7]([N:9]1[C:17]2[C:12](=[C:13]([O:21][CH:22]([CH2:28][OH:29])[CH2:23][OH:24])[CH:14]=[CH:15][C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 160049611-(4-Azidobutanoyl)-4-(1,3-diacetoxypropan-2-yloxy)-7-nitroindoline

Product 1

HCID 160049621-(4-Azidobutanoyl)-4-(1,3-dihydroxypropan-2-yloxy)-7-nitroindolineYield 78.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 26 (0.76 g, 1.7 mmol) in MeOH (85 mL), water (8.5 mL) and 1 M aq. NaOH (4.1 mL, 4.1 mmol) was stirred at room temperature for 2 min, quenched with 1 M citric acid (8.5 mL) and concentrated under reduced pressure to ˜20 mL. The solution was diluted with water (30 mL), washed with EtOAc (3×50 mL) and the combined organic washings were washed with saturated aq. NaHCO3 and brine, dried and evaporated to a brown viscous oil which after trituration with Et2O gave 27 (0.49 g, 78%) as yellow needles, mp 78-79° C. (EtOAc-hexanes); 1H NMR (500 MHz) δ 7.70 (d, J=9.2 Hz, 1H), 6.76 (d, J=9.2 Hz, 1H), 4.57 (quintet, J=4.8 Hz, 1H), 4.25 (d, J=8.1 Hz, 2H), 3.95 (dd, J=11.9, 4.8 Hz, 2H), 3.92 (dd, J=11.9, 4.8 Hz, 2H), 3.43 (t, J=6.4 Hz, 2H), 3.14 (t, J=8.0 Hz, 2H), 2.57 (t, J=6.9 Hz, 2H), 2.03 (t, J=7.6 Hz, 2H), 2.02 (quintet, J=6.4 Hz, 2H); HRMS (ESI) (m/z): Calcd for (C15H19N5O6+H)+, 366.1408. Found: 366.1427.

Workup

  1. customquenched with 1 M citric acid (8.5 mL)
  2. concentrationconcentrated under reduced pressure to ˜20 mL
  3. additionThe solution was diluted with water (30 mL)
  4. washwashed with EtOAc (3×50 mL)
  5. washthe combined organic washings were washed with saturated aq. NaHCO3 and brine
  6. customdried
  7. customevaporated to a brown viscous oil which after trituration with Et2O

Sources & evidence

ORD record
ord-1b0e3e4dfcfd42e7a49e166a86d96e5d
Source dataset
uspto-grants-2010_06
Patent number
US07737169B2

Reaction notes

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