Sodium Hydroxide → HCID 178503037, compound

HRID 1525306Notes

Reaction equation

HRID 1525306 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([NH:16][C@H:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:18]3[CH:23]=[CH:22][C:21]([P:24]([CH3:29])(=[O:28])[O:25]CC)=[CH:20][CH:19]=3)=[O:15])=[CH:9][N:8]=2)[CH:6]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([NH:16][C@H:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:18]3[CH:19]=[CH:20][C:21]([P:24]([CH3:29])(=[O:25])[OH:28])=[CH:22][CH:23]=3)=[O:15])=[CH:9][N:8]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476767HCID 178476767, compound

Product 1

HCID 178503037HCID 178503037, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of compound 29-a (4 g, 7.8 mmol) in 30 ml of dioxane was treated with 7 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. The mixture was then concentrated under vacuum and the resulting residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with conc. HCl to pH=1 and the expected product, 29-1, crashed out (700 mg of crude). The product can be further purified via prep-HPLC (152 mg, 5%). 1H NMR (300 MHz, CD3OD): δ 8.66 (s, 1H), 8.57 (d, 1H), 7.81 (d, 1H), 7.77 (m, 2H), 7.52 (m, 2H), 7.20 (m, 2H), 7.13 (m, 2H), 6.38 (s, 1H), 1.65 (d, 3H). (M+H)+=486.2.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. additionthe resulting residue was diluted with water
  3. washwashed with ethyl acetate
  4. customThe product can be further purified via prep-HPLC (152 mg, 5%)

Sources & evidence

ORD record
ord-e695e784a53c4f218610957e943ce71d
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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