Trifluoroacetic acid → HCID 178485663, compound

HRID 1386637Notes

Reaction equation

HRID 1386637 reaction equation
[NH:1]([C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])[C@H:2]([C:28]([N:30]([CH3:60])[C@H:31]([C:47]([NH:49][CH2:50][CH2:51]OCC1C=CC=CC=1)=[O:48])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)=[O:29])[CH2:3][C:4]1[N:8]=[CH:7][N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=1.C(O)(C(F)(F)F)=O.C(OCC)C.[CH3:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88]>C(Cl)Cl>[CH2:64]([O:63][C:61](=[O:62])[NH:1][CH:2]([C:28](=[O:29])[N:30]([CH:31]([C:47](=[O:48])[NH:49][CH2:50][CH2:51][C:85]1[CH:84]=[CH:83][CH:88]=[CH:87][CH:86]=1)[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)[CH3:60])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15546121HCID 15546121, compoundHCID 21584099Diethylether hexane

Product 1

HCID 178485663HCID 178485663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cbz-His(Trt)-NMe-Tyr(OBn)-NH—CH2—CH2-OBn (from Step 3, 0.5 g, 0.55 mmol) was treated with 50 mL of 50% TFA in methylene chloride. The solution was stirred at room temperature for 2 hours. The solvent was reduced in volume and diethyl ether/hexane (200 mL) was added to the residue. The solution was cooled to −40° C. overnight. The ether/hexane was decanted and the residue dried in vacuo. Purification was carried out by reverse-phase preparative HPLC (C-18) reverse-phase column, 20% to 60% of 0.1% TFA in acetonitrile against 0.1% TFA in water, 100 minutes, 13 mL/min) to give 37.5 mg of a white foam; MS-ES 661 (m+1).

Workup

  1. additionwas added to the residue
  2. temperatureThe solution was cooled to −40° C. overnight
  3. customThe ether/hexane was decanted
  4. customthe residue dried in vacuo
  5. customPurification
  6. customwas carried out by reverse-phase preparative HPLC (C-18) reverse-phase column, 20% to 60% of 0.1% TFA in acetonitrile against 0.1% TFA in water, 100 minutes, 13 mL/min

Sources & evidence

ORD record
ord-48cf5b84190a429098cd65302b45ae63
Source dataset
uspto-grants-2001_07
Patent number
US06265382B1

Reaction notes

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