Trifluoroacetic acid → HCID 59552575, compound

HRID 1170781Notes

Reaction equation

HRID 1170781 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-c0040754f93643aa95f7e8172c952469
Source dataset
uspto-grants-2010_11
Patent number
US07829063B2

Reaction notes

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