Ethylmorpholine → HCID 54486216, compound

HRID 1883496Notes

Reaction equation

[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[Br:23][C:24]1[CH:25]=[C:26]([CH:30]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[C:31]([OH:33])=O)[CH:27]=[CH:28][CH:29]=1.C(O)(=O)C.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][CH:57]([CH2:60][NH:61][C:62](=[O:71])[C@@H:63]([NH2:70])[CH:64]2[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]2)[CH2:56][CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48].C(N1CCOCC1)C>CN(C)C=O>[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][CH:57]([CH2:60][NH:61][C:62](=[O:71])[C@@H:63]([NH:70][C:31](=[O:33])[CH:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([Br:23])[CH:25]=2)[CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[CH:64]2[CH2:65][CH2:66][CH2:67][CH2:68][CH2:69]2)[CH2:56][CH2:55]1)=[O:53])([CH3:50])([CH3:48])[CH3:49]

Participants

Conditions

Temperature: 22 °C

Procedure

At 4° C., TOTU (1.59 g, 4.84 mmol) was added to a solution of 2-(3-bromo-phenyl)-3-(4-cyano-phenyl)-propionic acid (1.6 g, 4.84 mmol), 4-[(2-(S)-amino-2-cyclohexyl-acetylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester acetic acid salt (2.0 g, 4.84 mmol), and N-ethylmorpholine (1.2 ml, 9.68 mmol) in dimethylformamide (80 ml). The mixture was stirred at 22° C. for 15 hours, then evaporated in vacuo and stirred with sodium bicarbonate solution. The resulting precipitate was sucked off, washed with water, and dried in vacuo at 40° C. to give the desired product, which was used without further purification. MS m/z 665.2 (M+H+).

Workup

customevaporated in vacuo
stirringstirred with sodium bicarbonate solution
washwashed with water
customdried in vacuo at 40° C.

Sources & evidence

ORD record: ord-b8ca2b48c7354d0691edbfb212a0d04c
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759420B1

Reaction notes

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