HCID 178447096, compound → HCID 178511414, compound

HRID 2103935Notes

Reaction equation

HRID 2103935 reaction equation
C([C:5]([C:22](=[O:66])[C@H:23]([CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[NH:24][C:25](=[O:58])[C@H:26]([CH2:47][C:48](=[O:57])[O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[NH:27][C:28](=[O:46])[CH2:29][CH2:30][NH:31][C:32](=[O:45])[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[NH:40][O:41][C:42](=[O:44])[N:43]=2)=[CH:35][CH:34]=1)([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21])[C:6]([O-:8])=[O:7])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:41]1[C:42](=[O:44])[N:43]=[C:39]([C:36]2[CH:35]=[CH:34][C:33]([C:32]([NH:31][CH2:30][CH2:29][C:28]([NH:27][C@H:26]([C:25]([NH:24][C@H:23]([C:22]([CH:5]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21])[C:6]([OH:8])=[O:7])=[O:66])[CH2:59][C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)=[O:58])[CH2:47][C:48](=[O:57])[O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)=[O:46])=[O:45])=[CH:38][CH:37]=2)[NH:40]1

Participants

4

Reactant 1

HCID 178447096HCID 178447096, compound

Product 1

HCID 178511414HCID 178511414, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 11 (0.2 g, crude, max. 0.22 mmol) was stirred in a mixture of DCM (5 mL) and TFA (3 mL). After 2 h the solution was concentrated and remains of TFA were removed by repeated concentration in toluene (3×5 mL). The product was purified by preparative HPLC-MS to give compound 12 in pure form (0.11 g, 56% over the three steps from 9).

Workup

  1. concentrationAfter 2 h the solution was concentrated
  2. customwere removed
  3. concentrationconcentration in toluene (3×5 mL)
  4. customThe product was purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-3ea67829f5c440e7975d8e38df716d93
Source dataset
uspto-grants-2009_08
Patent number
US07576071B2

Reaction notes

Loading…