Lithium Hydroxide → HCID 57925948, compound

HRID 1013486Notes

Reaction equation

HRID 1013486 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[P:11]([O:15][CH3:16])([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.[Li+].[OH-]>O1CCOCC1.CCOC(C)=O>[C:21]([O:20][C:18]([NH:17][CH:10]([P:11]([O:15][CH3:16])([O:13][CH3:14])=[O:12])[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][CH:6]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57925992HCID 57925992, compound

Product 1

HCID 57925948HCID 57925948, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[tert-Butoxycarbonylamino-(dimethoxy-phosphoryl)-methyl]-benzoic acid methyl ester (150 mg, 0.402 mmol) was made 0.25 M in dioxane and to this stirring solution was added 3 M aq LiOH (29 mg, 1.205 mmol). The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with EtOAc and washed with 1N aq HCl. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was carried onto subsequent coupling without further purification: 1H NMR (DMSO-d6, 600 MHz) 12.68 (br-s, 1H), 8.07-8.13 (m, 1H), 7.84-7.92 (m, 2H), 7.50-7.61 (m, 2H), 5.15-5.25 (m, 1H), 3.46-3.63 (m, 6H), 1.36 (s, 9H).

Workup

  1. washwashed with 1N aq HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was carried onto subsequent coupling without further purification

Sources & evidence

ORD record
ord-6d1d44f14fc24c7194aebc075d990fa2
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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