Sodium hydride → HCID 58671550, compound

HRID 2221095

Reaction equation

HRID 2221095 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH:14](P(OCC)(OCC)=O)[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:27]([C:29]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:32]=[CH:31][C:30]=1[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=O>C1COCC1>[CH2:3]([O:10][C:11]([NH:13]/[C:14](=[CH:27]\[C:29]1[C:30]([NH:41][C:42]([O:43][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:48])=[CH:31][N:32]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:34]=1)/[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11068333Methyl 2-(((benzyloxy)carbonyl)amino)-2-(diethyl phosphono)acetateHCID 58671548HCID 58671548, compound

Product 1

HCID 58671550HCID 58671550, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a slurry of 60% of sodium hydride (228 mg, 5.7 mmol) in THF (17 mL) at 0° C. was added 1A (1.88 g, 5.24 mmol) in several portions over 10 min. The reaction mixture was then brought to RT for 20 min, then cooled again at 0° C. A suspension of 3C (1.42 g, 4.76 mmol) in THF (17 mL) was added over 10 min at 0C, then the reaction was warmed up to RT. After stirring for 20 min, the reaction was quenched with water (40 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined EtOAc extracts were dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (110 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as an off-white solid (1 g, 42%). LC/MS (method A): retention time=3.33 min, (M+H)+=504.

Workup

  1. temperaturethe reaction was warmed up to RT
  2. customthe reaction was quenched with water (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel (110 g) column chromatography
  8. washeluting with a gradient of EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-cb1e9c6501204994b1b53696e03a67be
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Linked notes

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