Ammonia → HCID 23567963, compound

HRID 1368834Notes

Reaction equation

HRID 1368834 reaction equation
Cl[CH2:2][C@H:3]([OH:18])[CH2:4][P:5]([C:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])[CH3:11])(=[O:9])[O:6][CH2:7][CH3:8].[NH3:19]>C(O)C>[NH2:19][CH2:2][C@H:3]([OH:18])[CH2:4][P:5]([C:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])[CH3:11])(=[O:9])[O:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23567962HCID 23567962, compound

Product 1

HCID 23567963HCID 23567963, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (2R)-(3-chloro-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate (5.0 g, 17 mmol) in ethanol containing 9% of ammonia was stirred in an autoclave at room temperature for 4 days and at 60° C. for one further day. The solution was evaporated and the residue was purified by chromatography on a wet-packed silica gel column eluting with methylene chloride/methanol (5-8% MeOH) containing 5% triethylamine. The appropriate fractions were combined, evaporated and diluted with methylene chloride and water. The aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3 and repeatedly extracted with methylene chloride. The combined organic layers were dried over Na2SO4 and evaporated to give 1.2 g (26%) of ethyl (2S)-(3-amino-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate as a clear oil. Data: 1H NMR (300 MHz, CDCl3) δ4.40-4.55 (b, 1H), 4.10-4.30 (m, 2H), 3.55-3.80 (m, 4H), 3.20-3.30 (m, 1H), 3.00-3.10 (m, 1H), 2.00-2.40 (m, 2H), 1.45-1.53 (dd, J=3.4, 11.7 Hz, 3H), 1.30-1.40 (m, 3H), 1.15-1.25 (m, 6H).

Workup

  1. customThe solution was evaporated
  2. customthe residue was purified by chromatography on a wet-packed silica gel column
  3. washeluting with methylene chloride/methanol (5-8% MeOH)
  4. additioncontaining 5% triethylamine
  5. customevaporated
  6. additiondiluted with methylene chloride and water
  7. additionThe aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3
  8. extractionrepeatedly extracted with methylene chloride
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-6700b3dd7c6049129302de89c9f42f19
Source dataset
uspto-grants-2003_06
Patent number
US06576626B2

Reaction notes

Loading…