Trifluoroacetic acid → HCID 131713587, compound

HRID 1462853Notes

Reaction equation

HRID 1462853 reaction equation
C(O)(C(F)(F)F)=O.[NH:8](C(OC(C)(C)C)=O)[C@H:9]([C:26]([NH:28][C@H:29]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:27])[CH2:10][C:11]1[N:15]=[CH:14][N:13]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=1>C(Cl)CCl>[NH2:8][C@H:9]([C:26]([NH:28][C@H:29]([C:45]([O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:27])[CH2:10][C:11]1[N:15]=[CH:14][N:13]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713588HCID 131713588, compound

Product 1

HCID 131713587HCID 131713587, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

160 ml of TFA was added to 86 g of Boc-His(Tos)-Lys(Z)-OBzl dissolved in 100 ml of ethylene chloride under cooling with ice, and the mixture was stirred at the same temperature for 30 minutes and at room temperature for an hour. The solvent and TFA were distilled off, chloroform was added to the residue, and neutralization was carried out with aqueous potassium carbonate. After the reaction mixture was washed with saturated saline, passed through silica gel and sodium sulfate anhydride columns, the solvent was distilled off. Then, methanol was added to precipitate crystals, which were filtered out and dried to obtain 61.2 g of His(Tos)-Lys(Z)-OBzl. (By this process, the product is obtained in the crystallized form).

Workup

  1. temperatureunder cooling with ice
  2. distillationThe solvent and TFA were distilled off
  3. additionchloroform was added to the residue, and neutralization
  4. washAfter the reaction mixture was washed with saturated saline
  5. distillationthe solvent was distilled off
  6. additionThen, methanol was added
  7. customto precipitate crystals, which
  8. filtrationwere filtered out
  9. customdried

Sources & evidence

ORD record
ord-a673c95f7ecd41a4a815bab9aed91a7e
Source dataset
uspto-grants-1984_07
Patent number
US04461724

Reaction notes

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