Diisopropylethylamine → HCID 57070558, compound

HRID 1263615Notes

Reaction equation

HRID 1263615 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:14]=1)[CH2:5][CH2:6][S:7]([CH3:10])(=O)=O.[CH2:25]([O:28][C:29]([N:31]1[CH2:35][C@@H:34]([S:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][C@H:32]1[CH2:44][NH2:45])=[O:30])[CH:26]=[CH2:27].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:25]([O:28][C:29]([N:31]1[CH2:35][C@@H:34]([S:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH2:33][C@H:32]1[CH2:44][NH:45][S:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:12](=[O:23])[NH:11][C@H:4]([C:3]([O:2][CH3:1])=[O:24])[CH2:5][CH2:6][S:7][CH3:10])[CH:14]=1)(=[O:21])=[O:20])=[O:30])[CH:26]=[CH2:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57282618HCID 57282618, compoundHCID 59048564HCID 59048564, compound

Product 1

HCID 57070558HCID 57070558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 15(a) (1.53 g. 4.18 mmol) in CH2Cl2 (20 mL) was added to a stirred solution of (2S,4S)-2-aminomethyl-4-BOCsulfanyl-pyrollidine-1-carboxylic acid allyl ester (15(b)) (prepared as described in International Patent Application WO 92/17480. see pages 39-41) (1.32 g. 4.18 mmol) and (iPr)2NEt (1.5 mL. 9.0 mmol) in CH2Cl2 (30 mL) at 0° C. under argon. The resulting solution was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was then washed with water (100 mL), dried over MgSO4, filtered and concentrated to a viscous white gum. This was then purified by flash chromatography on 9385 SiO2. eluting with a gradient of 35-50% EtOAc/i-Hexane to give (2S,4S)-4-BOCsulfanyl-2-{[3-([1S]-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-benzenesulfonylamino]-methyl }-pyrrolidine-1-carboxylic acid allyl ester (15(c)) as a colourless foam: 2.19 g (81.3%).

Workup

  1. washThe reaction mixture was then washed with water (100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a viscous white gum
  5. customThis was then purified by flash chromatography on 9385 SiO2
  6. washeluting with a gradient of 35-50% EtOAc/i-Hexane

Sources & evidence

ORD record
ord-38ab020f8de246ed9a8cb3822a9658a6
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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