Trifluoroacetic acid → HCID 54588736, compound

HRID 1944980Notes

Reaction equation

HRID 1944980 reaction equation
C(OC([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:82][Si](C(C)(C)C)(C)C)[CH2:21][N:22]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:81])[C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([S:55]([C:58]4[CH:59]=[C:60]5[C:65](=[C:66]([CH3:68])[CH:67]=4)[N:64]=[CH:63][C:62]([C:69](=[O:71])[NH2:70])=[C:61]5[NH:72][C:73]4[CH:78]=[CH:77][CH:76]=[C:75]([O:79][CH3:80])[CH:74]=4)(=[O:57])=[O:56])[CH:50]=3)=[CH:43][CH:42]=2)C(=O)OC(C)(C)C)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:82][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48]([C:49]2[CH:50]=[C:51]([S:55]([C:58]3[CH:59]=[C:60]4[C:65](=[C:66]([CH3:68])[CH:67]=3)[N:64]=[CH:63][C:62]([C:69]([NH2:70])=[O:71])=[C:61]4[NH:72][C:73]3[CH:78]=[CH:77][CH:76]=[C:75]([O:79][CH3:80])[CH:74]=3)(=[O:56])=[O:57])[CH:52]=[CH:53][CH:54]=2)=[O:81])=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659122HCID 86659122, compound

Product 1

HCID 54588736HCID 54588736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The concentrated reaction mixture containing Intermediate 159 was taken up in dichloromethane (5 mL) and treated with trifluoroacetic acid (1 mL). After stirring overnight at room temperature, the mixture was concentrated under reduced pressure. The residue was taken up in tetrahydrofuran (1 mL) and treated with TBAF solution (1.0 M in THF, 1 mL) and glacial acetic acid (0.30 mL). The mixture was stirred overnight in a 40° C. oil bath, and then concentrated under reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography (RP-HPLC, acetonitrile/water/0.1% TFA) to provide, after concentration, the trifluoroacetic acid salt of the title compound as a yellow powder (16 mg).

Workup

  1. customThe concentrated reaction mixture
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additiontreated with TBAF solution (1.0 M in THF, 1 mL) and glacial acetic acid (0.30 mL)
  4. stirringThe mixture was stirred overnight in a 40° C. oil bath
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse-phase high performance liquid chromatography (RP-HPLC, acetonitrile/water/0.1% TFA)
  7. customto provide
  8. concentrationafter concentration

Sources & evidence

ORD record
ord-aeeda67d470f44e2b0fa1febc5b7a002
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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