(2S)-3-Phenylpropane-1,2-diamine → HCID 178428030, compound

HRID 560914Notes

Reaction equation

HRID 560914 reaction equation
[C:1]1([CH2:7][C@H:8]([NH2:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.[F:16][C:17]1[CH:40]=[CH:39][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:31][C:30]([C:32](OCC)=O)=[C:29]([CH3:37])[CH:28]=3)[C:23]2=[O:38])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH2:7]([CH:8]1[CH2:9][NH:10][C:32]([C:30]2[S:31][C:27]([N:24]3[CH2:25][CH2:26][N:22]([CH2:21][C:20]4[CH:39]=[CH:40][C:17]([F:16])=[CH:18][CH:19]=4)[C:23]3=[O:38])=[CH:28][C:29]=2[CH3:37])=[N:11]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 12699301(2S)-3-Phenylpropane-1,2-diamineHCID 16682925TrimethylaluminumHCID 58031706Ethyl 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

Product 1

HCID 178428030HCID 178428030, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of (S)-3-phenylpropane-1,2-diamine (0.37 g, 2.48 mmol) in toluene (20 mL) at 0° C. under nitrogen atmosphere was added dropwise trimethylaluminum (1.24 mL of 2.0 M solution in toluene, 2.48 mmol). When the fuming ceased, ethyl 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate (0.60 g, 1.66 mmol) in toluene (5 mL) was added slowly. The resulting mixture was stirred at reflux for 18 h, cooled to ambient temperature and partitioned between ethyl acetate (75 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (3×75 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with dichloromethane/methanol/triethyl amine (9/1/0.1) to afford the title compound as brown viscous oil in 29% yield (0.06 g): MS (ES+) m/z 449.2 (M+1).

Workup

  1. temperatureat reflux for 18 h
  2. custompartitioned between ethyl acetate (75 mL) and water (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×75 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with dichloromethane/methanol/triethyl amine (9/1/0.1)

Sources & evidence

ORD record
ord-3b2f6c1820a643cfa8e117e9cdbe91d6
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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