Trifluoroacetic acid → HCID 131716519, compound

HRID 1709962Notes

Reaction equation

HRID 1709962 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:24][C@H:25]([C:31]([NH:33][C:34]1[CH:43]=[C:42]2[C:37]([C:38]([CH3:45])=[CH:39][C:40](=[O:44])[O:41]2)=[CH:36][CH:35]=1)=[O:32])[CH2:26][CH2:27][C:28](=[O:30])[NH2:29])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>C1(C)C=CC=CC=1>[NH2:1][C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:24][C@H:25]([C:31]([NH:33][C:34]1[CH:43]=[C:42]2[C:37]([C:38]([CH3:45])=[CH:39][C:40](=[O:44])[O:41]2)=[CH:36][CH:35]=1)=[O:32])[CH2:26][CH2:27][C:28](=[O:30])[NH2:29])=[O:23])[CH2:18][CH:19]([CH3:20])[CH3:21])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[F:53][C:54]([C:55]([OH:57])=[O:56])([F:59])[F:58]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131716516HCID 131716516, compound

Product 1

HCID 131716519HCID 131716519, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Boc-Phe-Gly-Leu-Gln-AMC (0.63 g) was deblocked by treatment with trifluoroacetic acid at about 23°. Toluene was added to the resulting reaction mixture, and then the combined solvents were evaporated at reduced pressure , leaving a residue. This residue was redissolved in toluene, and the solvent was then evaporated again to leave a residue, which was dried in vacuo overnight over solid potassium hydroxide to provide 0.69 g of white, solid H-Phe-Gly-Leu-Gln-AMC trifluoroacetate. TLC with 1-butanol:acetic acid: water (4:1:1) showed two spots, Rf 0.58 and Rf 0.51.

Workup

  1. customthe combined solvents were evaporated at reduced pressure
  2. customleaving a residue
  3. customthe solvent was then evaporated again
  4. customto leave a residue, which
  5. dry with materialwas dried in vacuo overnight over solid potassium hydroxide

Sources & evidence

ORD record
ord-45181daf199e42c8940a757e326fe20f
Source dataset
uspto-grants-1990_08
Patent number
US04952493

Reaction notes

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