Hydrochloric Acid → HCID 57798931, compound

HRID 2100370Notes

Reaction equation

HRID 2100370 reaction equation
[Li+].[OH-].[CH2:3]([O:10][P:11]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31]C)=[O:30])=[CH:24][CH:23]=1)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C1COCC1.CO>[CH2:14]([O:13][P:11]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:26][CH:27]=1)([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57799050Methyl 2-(4-(bis(benzyloxy)phosphoryloxy)phenyl)acetate

Product 1

HCID 57798931HCID 57798931, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

LiOH (1N, 9 mL, 5 mmol) was added into a mixture of methyl 2-(4-(bis(benzyloxy)phosphoryloxy)phenyl)acetate (1.53 g, 3.59 mmol) in THF (15 mL) and methanol (5 mL) at 0° C. The reaction was stirred at 0° C. for 3.5 h, than 0.5 h at rt. The reaction was monitored by LC-MS until the hydrolysis was completed. The mixture was cooled to 0° C. and acidified by 1N HCl to pH=2. The mixture was concentrated and extracted by ethyl acetate (50 mL×3). The extraction was dried over Na2SO4 and concentrated to dryness to give the acid (1.5 g, 67.6% yield) as a light yellow oil.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. concentrationThe mixture was concentrated
  3. extractionextracted by ethyl acetate (50 mL×3)
  4. extractionThe extraction
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-89fd13e94fe64bdab7bb54fb1fab9646
Source dataset
uspto-grants-2009_08
Patent number
US07572795B2

Reaction notes

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