1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58997967, compound

HRID 1593264Notes

Reaction equation

HRID 1593264 reaction equation
[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].[F:23][C:24]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:25]=1[CH:26]=O.C1CCN2C(=NCCC2)CC1>ClCCl>[CH2:10]([O:9][C:7]([NH:6]/[C:5](=[CH:26]\[C:25]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:24]=1[F:23])/[C:3]([O:2][CH3:1])=[O:4])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1376632,5-DifluorobenzaldehydeHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate

Product 1

HCID 58997967HCID 58997967, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (6.1 g) and 2,5-difluorobenzaldehyde (2.0 g) in dry dichloromethane (60 mL), was treated dropwise with a solution of DBU (2.5 mL) in dichloromethane (20 mL). The mixture was stirred at room temperature for 2 h, then was concentrated to approximately 20 mL and partitioned between ethyl acetate (150 mL) and 1N hydrochloric acid (50 mL). The organic extract was collected, consecutively washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine, dried (sodium sulfate), filtered and evaporated. The crude product (6.5 g) was purified by flash chromatography (20% ethyl acetate/hexanes) to yield the title compound (4.0 g, 82%). 1H NMR (300 MHz, CDCl3) δ 3.85 (s, 3H), 5.10, (s, 2H), 6.60 (bs, 1H), 6.9-7.1 (m, 2H), 7.21 (m, 1H), 7.2-7.3 (m, 6H). MS APCI, m/z=348 (M+1). LC/MS: 2.53 min.

Workup

  1. concentrationwas concentrated to approximately 20 mL
  2. custompartitioned between ethyl acetate (150 mL) and 1N hydrochloric acid (50 mL)
  3. extractionThe organic extract
  4. customwas collected
  5. washconsecutively washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product (6.5 g) was purified by flash chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-56fba16782c74acd9adb2fe8191b6284
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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