Diisopropylamine → (2S)-2-{[(S)-4-methoxyphenylsulfinyl]acetyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine

HRID 1720492Notes

Reaction equation

HRID 1720492 reaction equation
C(NC(C)C)(C)C.[CH3:8][S@@:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:10].C([O:26][C:27](=O)[C@@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[C:33](=[O:49])[C@@H:34]1[CH2:38][CH2:37][CH2:36][N:35]1[C:39](=[O:48])[CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)C1C=CC=CC=1>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([S@:9]([CH2:8][C:27]([C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2[C:33](=[O:49])[C@@H:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39](=[O:48])[CH2:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:26])=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 12072511(S)-(-)-4-methoxyphenyl methyl sulfoxideHCID 54563213N-(3-Phenylpropionyl)-L-prolyl-L-proline benzyl ester

Product 1

HCID 54211729(2S)-2-{[(S)-4-methoxyphenylsulfinyl]acetyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidineYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To diisopropylamine (0.13 ml) in THF (8 ml) was dropwise added 1.62M n-butyllithium-hexane solution (1.2 ml) at -78° C., followed by stirring at 0° C. for 0.5 hour. The reaction mixture was cooled to -30° C., dropwise added with (S)-(-)-4methoxyphenyl methyl sulfoxide (157 mg) in THF (8 ml), and stirred at 0° C. for 0.5 hour. The reaction mixture was cooled to -78° C., added with N-(3-phenylpropionyl)-L-prolyl-L-proline benzyl ester (400 mg) in THF (8 ml) quickly, and stirred for 0.5 hour. The reaction mixture was treated as in Example 13-A) and the residue obtained was purified by medium pressure liquid chromatography (silica gel, eluate; chloroform:methanol=99:1) to give 195 mg of the title compound (See Table 5).

Workup

  1. customat -78° C.
  2. temperatureThe reaction mixture was cooled to -30° C.
  3. stirringstirred at 0° C. for 0.5 hour
  4. temperatureThe reaction mixture was cooled to -78° C.
  5. stirringstirred for 0.5 hour
  6. additionThe reaction mixture was treated as in Example 13-A) and the residue
  7. customobtained
  8. customwas purified by medium pressure liquid chromatography (silica gel, eluate; chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-39167d6b74744c1a970f4fa64fce412b
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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