P-Cresol → HCID 178461611, compound

HRID 369022Notes

Reaction equation

HRID 369022 reaction equation
[NH:1]1[C:60](=[O:61])[C@H:49]([CH2:50][C:51]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[NH:53][CH:52]=2)[NH:48][C:46](=[O:47])[C@@H:44]([CH3:45])[NH:43][C:41](=[O:42])[C@H:33]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[NH:32][C:30](=[O:31])[C@@H:12]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:29])[NH:18]S(C2C=CC(C)=CC=2)(=O)=O)[NH:11][C:9](=[O:10])[C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C(O)=CC=C(C)C=1>C(S)(S)C>[NH:1]1[C:60](=[O:61])[C@H:49]([CH2:50][C:51]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[NH:53][CH:52]=2)[NH:48][C:46](=[O:47])[C@@H:44]([CH3:45])[NH:43][C:41](=[O:42])[C@H:33]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:32][C:30](=[O:31])[C@@H:12]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:18])[NH2:29])[NH:11][C:9](=[O:10])[C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2879P-CresolHCID 178427498HCID 178427498, compound

Product 1

HCID 178461611HCID 178461611, compound

Reagents, catalysts & solvents 1

HCID 336451,1-EthanedithiolSolvent

Procedure

The crude cyclo(-Phg-D-Arg(Tos)-Phe-D-Ala-Trp-) (100 mg) as obtained in Example 48 was treated with HF in the presence of p-cresol (75 mg) and ethanedithiol (50 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, 20 g 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(-Phg-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, 20 g 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-16eea3f005f1441099b2c61c3122f49a
Source dataset
uspto-grants-2000_10
Patent number
US06136781

Reaction notes

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