Trifluoroacetic acid → HCID 68310556, compound

HRID 529580Notes

Reaction equation

C(O)(C(F)(F)F)=O.[CH2:8]([C@@H:15]([CH2:38][CH2:39][C@H:40]([CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:41]([NH:43][C@@H:44]1[C:50](=[O:51])[N:49]2[C@H:52]([C:56]([O:58]C(C)(C)C)=[O:57])[CH2:53][CH2:54][CH2:55][N:48]2[CH2:47][CH2:46][CH2:45]1)=[O:42])[C:16]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]2[C@H:27]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:28][CH2:29][CH2:30][N:23]2[CH2:22][CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([C@@H:15]([CH2:38][CH2:39][C@H:40]([CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:41]([NH:43][C@@H:44]1[C:50](=[O:51])[N:49]2[C@H:52]([C:56]([OH:58])=[O:57])[CH2:53][CH2:54][CH2:55][N:48]2[CH2:47][CH2:46][CH2:45]1)=[O:42])[C:16]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]2[C@H:27]([C:31]([OH:33])=[O:32])[CH2:28][CH2:29][CH2:30][N:23]2[CH2:22][CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86706242HCID 86706242, compound

Product 1

HCID 68310556HCID 68310556, compoundYield 101%

Procedure

TFA (0.075 mL) was added to a solution of di-tert-butyl (1S,9S,1′S,9′S)-9,9′-(((2R,5R)-2,5-dibenzyl-1,6-dioxo-1,6-hexanediyl)diimino)bis(10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate) (28 mg, 0.033 in DCM, 0.25 mL). The reaction mixture was stirred overnight at rt. The reaction mixture was concentrated and placed under vacuum to give (1S,9S,1′S,9′S)-9,9′-(((2R,5R)-2,5-dibenzyl-1,6-dioxo-1,6-hexanediyl)diimino)bis(10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid) (25 mg, 0.033 mmol, 100% yield). Anal. Calcd. for C40H52N6O8 m/z 744.8. found: 745.6 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-116d38d49a1441798f07072839dac78d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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