Dimethyl Sulfide → HPro-DTrp-Phe-DTrp-Leu-MetNH2

HRID 2418581Notes

Reaction equation

HRID 2418581 reaction equation
[N:1]1(C(OC(C)(C)C)=O)C[CH2:62][CH2:61][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54]CSC)=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].FC(F)(F)C(O)=O.[CH:78](S)(S)[CH3:79].[CH3:82][S:83][CH3:84]>>[NH:1]1[CH2:79][CH2:78][CH2:62][CH2:61][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:82][S:83][CH3:84])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 4

HCID 1068Dimethyl SulfideHCID 6422Trifluoroacetic acidHCID 336451,1-EthanedithiolHCID 131713765HCID 131713765, compound

Product 1

HCID 131713764HPro-DTrp-Phe-DTrp-Leu-MetNH2

Conditions

Temperature
0 °C

Procedure

BocPro-DTrp-Phe-DTrp-Leu-MetNH2 (2.45 mmole.) was added to a solution of trifluoroacetic acid (18 ml.), dimethylsulfide (20 ml.) and ethanedithiol (1.8 ml.) with cooling to 0° C. The mixture was allowed to warm to room temperature, stirred for one hour, and stripped of volatiles. The residue was washed with hexane, then with ether, then purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel using methanol-water (75:25) containing ammonium acetate (0.2%) as eluant. Conversion of the product to the phosphate salt by ion exchange and lyophilization afforded HPro-DTrp-Phe-DTrp-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt hydrate (2:7) in 62% yield (1.63 g.).

Workup

  1. temperatureto warm to room temperature
  2. washThe residue was washed with hexane
  3. customwith ether, then purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel
  4. additioncontaining ammonium acetate (0.2%) as eluant

Sources & evidence

ORD record
ord-3093f3cf950340d99af6f0ef45242e58
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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