Trifluoroacetic acid → HCID 178502463, compound

HRID 1804664Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:66])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][C@H:14]([O:16]C(C)(C)C)[CH2:13][C@H:12]1[C:21]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]4[CH:65]=[CH:64][C:39]5[NH:40][C:41]([C@@H:43]6[CH2:47][C@@H:46]([O:48]C(C)(C)C)[CH2:45][N:44]6[C:53](=[O:63])[C@@H:54]([NH:58][C:59]([O:61][CH3:62])=[O:60])[CH:55]([CH3:57])[CH3:56])=[N:42][C:38]=5[CH:37]=4)=[CH:32][CH:31]=3)=[CH:29][C:23]=2[N:22]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].C(O)(C(F)(F)F)=O>>[CH3:62][O:61][C:59](=[O:60])[NH:58][C@H:54]([C:53]([N:44]1[CH2:45][C@H:46]([OH:48])[CH2:47][C@H:43]1[C:41]1[NH:40][C:39]2[CH:64]=[CH:65][C:36]([C:33]3[CH:32]=[CH:31][C:30]([C:28]4[CH:27]=[CH:26][C:24]5[NH:25][C:21]([C@@H:12]6[CH2:13][C@@H:14]([OH:16])[CH2:15][N:11]6[C:9](=[O:10])[C@@H:5]([NH:4][C:3]([O:2][CH3:1])=[O:66])[CH:6]([CH3:8])[CH3:7])=[N:22][C:23]=5[CH:29]=4)=[CH:35][CH:34]=3)=[CH:37][C:38]=2[N:42]=1)=[O:63])[CH:55]([CH3:56])[CH3:57]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178502455HCID 178502455, compound

Product 1

HCID 178502463HCID 178502463, compoundYield 134.2%

Procedure

To a solution of compound from example 25 (15 mg, 0.015 mmol) is added TFA (0.3 mL) at 0° C. The reaction mixture is stirred 1 hour at rt, concentrated to dryness, and triturated with DCM (3×) to give title compound (16 mg).

Workup

concentrationconcentrated to dryness
customtriturated with DCM (3×)

Sources & evidence

ORD record: ord-a7e08ab088854c288a370609622ba459
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354419B2

Reaction notes

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