Sodium Hydroxide → HCID 178521677, compound

HRID 444687Notes

Reaction equation

HRID 444687 reaction equation
[C:1]12([NH:11][C:12](=[O:32])[NH:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([O:20]C(=O)C4C=CC([N+]([O-])=O)=CC=4)[CH2:16][CH2:15]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+]>C1COCC1>[OH:20][C@@H:17]1[CH2:18][CH2:19][C@H:14]([NH:13][C:12]([NH:11][C:1]23[CH2:2][CH:3]4[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]4)[CH2:10]2)[CH2:8]3)=[O:32])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178521681HCID 178521681, compound

Product 1

HCID 178521677HCID 178521677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester 1076 (1 g, 2.3 mmol) in THF (100 mL) was added 1N NaOH solution (4.6 mL, 4.6 mmol) at room temperature. The reaction mixture was stirred overnight, at which time the reaction was quenched by addition of 1N HCl solution (5.5 mL). The resulting white precipitate was collected by filtration and recrystallized from methanol/water. Yield: 0.63 g (95% of theory). M.P.: 205° C. 1H NMR (300 MHz, DMSO-d6): δ 5.67 (d, J=8.2 Hz, 1H), 5.45 (s, 1H), 4.41 (s, 1H), 3.63-3.51 (m, 1H), 3.46-3.36 (m, 1H), 2.00-1.92 (m, 3H), 1.87-1.72 (m, 6H), 1.66-1.28 (m, 14H).

Workup

  1. customwas quenched by addition of 1N HCl solution (5.5 mL)
  2. filtrationThe resulting white precipitate was collected by filtration
  3. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-0badc39f05c24d0c99f3408328929556
Source dataset
uspto-grants-2013_07
Patent number
US08476043B2

Reaction notes

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