Trifluoroacetic acid → HCID 131713590, compound

HRID 1462855Notes

Reaction equation

HRID 1462855 reaction equation
C(O)(C(F)(F)F)=O.[NH:8](C(OC(C)(C)C)=O)[C@H:9]([C:19]([NH:21][C@H:22]([C:39]([NH:41][C@H:42]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:40])[CH2:23][C:24]1[N:28]=[CH:27][N:26]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:25]=1)=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[NH2:8][C@H:9]([C:19]([NH:21][C@H:22]([C:39]([NH:41][C@H:42]([C:58]([O:60][CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)=[O:59])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:49])=[O:40])[CH2:23][C:24]1[N:28]=[CH:27][N:26]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:30])=[O:31])[CH:25]=1)=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713589HCID 131713589, compound

Product 1

HCID 131713590HCID 131713590, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 ml of TFA was added to 87.7 g of Boc-Ser(Bzl)-His(Tos)-Lys(Z)-OBzl dissolved in 130 ml of methylene chloride under cooling with ice, and the mixture was stirred at the same temperature for an hour and then at room temperature for an hour. Thereafter, procedures similar to those in (iv) in Example 1 were conducted to obtain 75.5 g of Compound 1.

Workup

  1. temperatureunder cooling with ice
  2. waitat room temperature for an hour

Sources & evidence

ORD record
ord-463a4a75e71e4a80af7a695f6ccfb545
Source dataset
uspto-grants-1984_07
Patent number
US04461724

Reaction notes

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