P-Cresol → HCID 178461612, compound

HRID 369021Notes

Reaction equation

HRID 369021 reaction equation
[NH:1]1[C:62](=[O:63])[C@H:51]([CH2:52][C:53]2[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[NH:55][CH:54]=2)[NH:50][C:48](=[O:49])[C@@H:46]([CH3:47])[NH:45][C:43](=[O:44])[C@H:35]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[NH:34][C:32](=[O:33])[C@@H:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:31])[NH:20]S(C2C=CC(C)=CC=2)(=O)=O)[NH:13][C:11](=[O:12])[C@@H:2]1[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.C1C(O)=CC=C(C)C=1>C(S)(S)C>[NH:1]1[C:62](=[O:63])[C@H:51]([CH2:52][C:53]2[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[NH:55][CH:54]=2)[NH:50][C:48](=[O:49])[C@@H:46]([CH3:47])[NH:45][C:43](=[O:44])[C@H:35]([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:34][C:32](=[O:33])[C@@H:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:20])[NH2:31])[NH:13][C:11](=[O:12])[C@@H:2]1[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 2879P-CresolHCID 178427499HCID 178427499, compound

Product 1

HCID 178461612HCID 178461612, compound

Reagents, catalysts & solvents 1

HCID 336451,1-EthanedithiolSolvent

Procedure

The crude cyclo(-pClPhe-D-Arg(Tos)-Phe-D-Ala-Trp-) (100 mg) as obtained in Example 38 was treated with HF in the presence of p-cresol (100 mg) and ethanedithiol (100 ml) for 2 hours, while cooling with ice. After HF was removed by distillation, ether was added to the residue and the precipitate formed was collected by filtration. This was purified by gel chromatography (G-25; 2 cm×80 cm). Finally, 1/5 of the product was further purified by HPLC using a column for partitioning purification of D-ODS-5-ST (2 cm×15 cm; produced by YMC Co.) to obtain cyclo(-pClPhe-D-Arg-Phe-D-Ala-Trp-).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter HF was removed by distillation, ether
  3. additionwas added to the residue
  4. customthe precipitate formed
  5. filtrationwas collected by filtration
  6. customThis was purified by gel chromatography (G-25; 2 cm×80 cm)
  7. customFinally, 1/5 of the product was further purified by HPLC
  8. customfor partitioning
  9. custompurification of D-ODS-5-ST (2 cm×15 cm; produced by YMC Co.)

Sources & evidence

ORD record
ord-5cfe3c6d3c344909ada0cdbbf302498c
Source dataset
uspto-grants-2000_10
Patent number
US06136781

Reaction notes

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