Lithium hydroxide, monohydrate → 4-(Bis-benzyloxy-phosphoryl)-butyric acid

HRID 902935Notes

Reaction equation

HRID 902935 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][P:8]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])C.O.[OH-].[Li+]>C1COCC1.O>[CH2:19]([O:18][P:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:26])=[O:3])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 109269054-(Bis-benzyloxy-phosphoryl)-butyric acid ethyl ester

Product 1

HCID 117598264-(Bis-benzyloxy-phosphoryl)-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of example 73 (8.66 g, 23.02 mmol) in THF (150 mL) was treated drop wise with a solution of lithium hydroxide-mono hydrate (1.97 g, 46.04 mmol) in water (150 mL). The reaction was complete after about 1 h, according to TLC analysis. Most of the solvent was evaporated. The residue was partitioned between water and ether. The organic phase was separated and the alkaline phase was extracted again with ether. It was next acidified with HCl (6M) to pH˜1 followed by several extractions with ethyl acetate. The recombined organic layer was dried over sodium sulfate, filtered, and evaporated to give the product as colorless oil. 1H-NMR(CDCl3, 400 MHz: 1.88(m, 4H); 2.40(t, J=6.9 Hz, 2H); 4.97, 4.96, 5.05(2dd, J1=11.8 Hz. J2=8.11 Hz, 4H); 7.35(m, 10H). 31P-NMR(CDCl3, 400 MHz): 33.15.

Workup

  1. customMost of the solvent was evaporated
  2. customThe residue was partitioned between water and ether
  3. customThe organic phase was separated
  4. extractionthe alkaline phase was extracted again with ether
  5. extractionfollowed by several extractions with ethyl acetate
  6. dry with materialThe recombined organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6dfb209be9614a54a3dc2b0afbcd03ee
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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