Trifluoroacetic acid → HCID 59552575, compound

HRID 1803815Notes

Reaction equation

HRID 1803815 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@@H:16]([CH2:61][OH:62])[C:17]([NH:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]([CH:58]=[CH:59][CH:60]=1)[CH2:26][O:27][CH2:28][C@H:29]([NH:34][C:35](=[O:57])[CH2:36][N:37]1[CH:41]=[C:40]([CH2:42][O:43][C:44]2[CH:56]=[CH:55][C:47]3[N:48]=[C:49]([S:51](=[O:54])(=[O:53])[NH2:52])[S:50][C:46]=3[CH:45]=2)[N:39]=[N:38]1)[C:30]([O:32]C)=[O:31])=[O:18])=O)(C)(C)C>C(Cl)Cl>[NH2:15][C@@H:16]([CH2:61][OH:62])[C:17]([NH:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]([CH:58]=[CH:59][CH:60]=1)[CH2:26][O:27][CH2:28][C@H:29]([NH:34][C:35](=[O:57])[CH2:36][N:37]1[CH:41]=[C:40]([CH2:42][O:43][C:44]2[CH:56]=[CH:55][C:47]3[N:48]=[C:49]([S:51](=[O:53])(=[O:54])[NH2:52])[S:50][C:46]=3[CH:45]=2)[N:39]=[N:38]1)[C:30]([OH:32])=[O:31])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68771037HCID 68771037, compound

Product 1

HCID 59552575HCID 59552575, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 mL vial with magnetic stir bar was added DCM (0.5 mL) and TFA (0.5 mL). To this, compound 70 was added and let to react for 30 min. After the completion of the reaction, solvents were removed in vacuo, THF was added (0.2 mL) followed by aq. LiOH (0.4 mL) and the reaction stirred for 30 min. After completion of the reaction, THF was removed and the crude residue was purified by HPLC to afford VM3163 (33%) as a colorless solid. LCMS for C27H32N8O10S2, calc'd: 692.17. found: 693.0 (M+H).

Workup

  1. customto react for 30 min
  2. customAfter the completion of the reaction, solvents
  3. customwere removed in vacuo, THF
  4. additionwas added (0.2 mL)
  5. customAfter completion of the reaction, THF
  6. customwas removed
  7. customthe crude residue was purified by HPLC
  8. customto afford VM3163 (33%) as a colorless solid

Sources & evidence

ORD record
ord-b84d5e0ef7014a1caa50671492af11fa
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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