1,1,3,3-Tetramethylguanidine → HCID 58864231, compound

HRID 1177809Notes

Reaction equation

HRID 1177809 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].CN(C)C(N(C)C)=N.[CH3:31][C:32]1[CH:33]=[C:34]([CH:37]=[C:38]([N+:43]([O-:45])=[O:44])[C:39]=1[N+:40]([O-:42])=[O:41])[CH:35]=O>O1CCCC1>[CH3:1][O:2][C:3](/[C:5](/[NH:6][C:7](=[O:8])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[CH:35]/[C:34]1[CH:37]=[C:38]([N+:43]([O-:45])=[O:44])[C:39]([N+:40]([O-:42])=[O:41])=[C:32]([CH3:31])[CH:33]=1)=[O:4]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 21102169HCID 21102169, compound

Product 1

HCID 58864231HCID 58864231, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(benzyloxycarbonyl)-α-phophonoglycine trimethyl ester (2.4 g, 7.3 mmol) in tetrahydrofuran (40 mL) at −78° C. was added 1,1,3,3-tetramethylguanidine (729 mg, 6.33 mmol) and the mixture was stirred for 1 h at −78° C. To this mixture was added a solution of 3-methyl-4,5-dinitrobenzaldehyde (1.4 g, 6.7 mmol) in tetrahydrofuran (15 mL). The reaction mixture was allowed to slowly warm to room temperature and was then stirred for 16 h at room temperature. The solvent was evaporated and the residue subjected to flash column chromatography (gradient, 1:2 to 1:1 ethyl acetate/hexanes). The product was then recrystallized from ethyl acetate/hexanes (1:1) to give the title compound (1.7 g, 62% yield). 1H-NMR (CDCl3, 300 MHz) δ 8.01 (s, 1H), 7.55 (s, 1H), 7.33-7.22 (m, 6H), 6.94 (bs, 1H), 5.06 (s, 2H), 3.89 (s, 3H), 2.29 (s, 3H). 13C-NMR (CDCl3, 75 MHz) δ 164.7, 152.5, 143.1, 140.6, 137.7, 137.0, 135.3, 132.5, 128.8, 128.7, 128.6, 127.1, 123.5, 123.2, 68.3, 53.5, 17.4. Mass spec.: 414.20 (MH)−.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringwas then stirred for 16 h at room temperature
  3. customThe solvent was evaporated
  4. customThe product was then recrystallized from ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-221ddf2f20f24a5986d0ebed66071180
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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