1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86604643, compound

HRID 1593310Notes

Reaction equation

HRID 1593310 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].[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=O)[S:27][CH:28]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[CH2:10]([O:9][C:7]([NH:6]/[C:5](=[CH:29]\[C:26]1[S:27][CH:28]=[C:24]([CH3:23])[CH:25]=1)/[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 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 27955264-methylthiophene-2-carbaldehyde

Product 1

HCID 86604643HCID 86604643, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (5.01 g, 15.1 mmol) and 4-methylthiophene-2-carbaldehyde (95a) (2.50 g, 19.8 mmol) in dry dichloromethane (100 mL) was cooled to 0° C. and treated dropwise with DBU (2.76 g, 18.1 mmol). The mixture was warmed to ambient temperature and stirred overnight. The solution was concentrated, taken up in ethyl acetate (150 mL) and washed with 5% hydrochloric acid (2×100 mL). The organic extract was washed with saturated aqueous sodium bicarbonate (2×150 mL), water (200 mL), dried (magnesium sulfate), filtered and evaporated. The residue was purified by crystallization from 4:1 (v/v) ethyl acetate/hexanes to afford the title compound (3.38 g, 67%) as the sole product. 1H NMR (300 MHz, d6-DMSO) δ2.20 (s, 3H), 3.70, (s, 3H), 5.12 (s, 2H), 7.20-7.52 (m, 7H), 7.69 (s, 1H), 8.82 (s, 1H). MS APCI, m/z=354 (M+Na). LC/MS: 2.43 min.

Workup

  1. concentrationThe solution was concentrated
  2. washwashed with 5% hydrochloric acid (2×100 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium bicarbonate (2×150 mL), water (200 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by crystallization from 4:1 (v/v) ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5c7c3f571d3940439fc622508851e781
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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