Lithium Hydroxide → HCID 57155448, compound

HRID 976237Notes

Reaction equation

HRID 976237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:13][C@@H:14]2[C:19]3[CH:20]=[C:21]([P:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])[O:25]C)[CH:22]=[CH:23][C:18]=3[O:17][C:16]([CH3:35])([CH3:34])[C@H:15]2[OH:36])=[N:10][C:11]#[N:12])=[CH:4][CH:3]=1.[Li+].[OH-]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:10][C:11]#[N:12])=[N:13][C@@H:14]2[C:19]3[CH:20]=[C:21]([P:24]([OH:27])([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])[CH:22]=[CH:23][C:18]=3[O:17][C:16]([CH3:35])([CH3:34])[C@H:15]2[OH:36])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 178502939HCID 178502939, compound

Product 1

HCID 57155448HCID 57155448, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Example 1 (152 mg, 0.29 mmol) in 1.5 mL of methanol was added 1.5 mL of 1M aq LiOH solution at room temperature. The reaction mixture was stirred for 18 hours (~1/2 complete by TLC) then an additional 1.5 mL of 1M aq LiOH solution was added. After 18 hours (complete by TLC) the reaction mixture was chromatographed (HP-20, 15×1.5 cm) eluting successively with 100 mL portions of water, 20% aq acetone and 40% aq acetone. The product containing fractions were combined, concentrated in vacuo then lyophilized to afford the title compound as a white solid (165 mg, 0.29 mmol, 100%). [α]D =+25° (c=0.17 in MeOH).

Workup

  1. customAfter 18 hours (complete by TLC) the reaction mixture was chromatographed (HP-20, 15×1.5 cm)
  2. washeluting successively with 100 mL portions of water, 20% aq acetone and 40% aq acetone
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-513dd40481f84196ab2716596b035c03
Source dataset
uspto-grants-1997_03
Patent number
US05612323

Reaction notes

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