Lithium hydroxide, monohydrate → HCID 18519020, compound

HRID 1369273Notes

Reaction equation

HRID 1369273 reaction equation
C[O:2][C:3](=[O:36])[CH:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])[CH:7]=1.O.[OH-].[Li+]>C1COCC1.O>[CH2:23]([O:22][P:20]([C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[C:3]([OH:36])=[O:2])[CH:11]=[CH:10][C:9]=1[P:12]([O:14][CH2:15][CH3:16])([O:17][CH2:18][CH3:19])=[O:13])([O:25][CH2:26][CH3:27])=[O:21])[CH3:24]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86585966HCID 86585966, compound

Product 1

HCID 18519020HCID 18519020, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3,4-Bis-(diethoxy-phosphoryl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (110 mg, 0.2 mmol) in 5 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (8.5 mg, 0.2 mmol) in 1.0 mL of water. The reaction mixture was stirred at 0° C. for 1 h. THF was removed under reduced pressure to a yellow oil which was diluted with 10 mL of 1 N HCl. The aqueous phase was extracted with CH2Cl2 (2×15 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford an oil 107 mg (100%). MS [M−H]− 537.

Workup

  1. customTHF was removed under reduced pressure to a yellow oil which
  2. additionwas diluted with 10 mL of 1 N HCl
  3. extractionThe aqueous phase was extracted with CH2Cl2 (2×15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ff635dab53549c7a9d33dd2f0903505
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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