Lithium hydroxide, monohydrate → HCID 15677395, compound

HRID 1087242Notes

Reaction equation

HRID 1087242 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C3C=CC=CC=3)[C@@H:13]([O:14]C(=O)C)[C@@H:12]2[F:30])=[C:4]([NH2:31])[N:3]=1.CC#N.O.O.[OH-].[Li+]>C(O)(=O)C>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@@H:12]2[F:30])=[C:4]([NH2:31])[N:3]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 15719371HCID 15719371, compoundHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 15677395HCID 15677395, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 1f (430 mg, 0.99 mmol) in 1:1 MeCN-H2O (40 mL) was treated in one portion with solid lithium hydroxide monohydrate (125 mg, 2.97 mmol). The reaction became a clear solution after being stirred at room temperature for 20 minutes. A 3-h TLC aliquot showed the deblocking to be Glacial acetic acid (57 μl) was added, and the solution was evaporated until white solid deposited. After being chilled, the solid was collected, washed with cold water, and dried in vacuo at room temperature to give crude 1g, 252 mg. This solid was dissolved in 40 mL of water and applied to a water-equilibrated SM-4 Bio-Bead column (1.5×32 cm). After initial elution with water, the product was eluted with a stepwise gradient, 5% →20% EtOH in water. The residue from the combined, evaporated column fractions was crystallized from 25 mL of boiling water with charcoal treatment and dried in vacuo at 56° C. for 16 hours to give pure 1g: 178 mg (59%). Mp 207°-209° C.; TLC 5:1 CHCl3 -MeOH, Rf 0.50; HPLC 99%, 9:1 H2O-MeCN; MS, z/e 288 (M+1)+ ; UV λ max pH 1 261 (14.0), 268 (sh), pH 7 260 (15.1), 268 (sh), pH 13 261 (14.9), 268 (sh). Anal. Calcd. for C10H11F2N5O3 ·H2O: C, 39.35; H, 4.29; N, 22.94. Found: C, 39.51; H, 4.21; N, 22.94.

Workup

  1. additionwas added
  2. customthe solution was evaporated until white solid
  3. temperatureAfter being chilled
  4. customthe solid was collected
  5. washwashed with cold water
  6. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-02090b5fd9cb435f929a0e78b931642a
Source dataset
uspto-grants-1991_07
Patent number
US05034518

Reaction notes

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