Hydrogen Bromide → HCID 86708778, compound

HRID 1751575Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:67])[NH:4][C@@H:5]([CH:64]([CH3:66])[CH3:65])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[NH:38][C:37]([C@@H:39]6[CH2:43][CH2:42][CH2:41][N:40]6[C:44](=[O:63])[C@@H:45]([NH:52]C(OCC6C=CC=CC=6)=O)[CH:46]6[CH2:51][CH2:50][S:49][CH2:48][CH2:47]6)=[N:36][CH:35]=5)=[CH:30][CH:29]=4)[CH:24]=3)[CH:19]=2)=[CH:16][N:17]=1)=[O:7].Br>C(#N)C.CC(O)=O>[NH2:52][C@@H:45]([CH:46]1[CH2:47][CH2:48][S:49][CH2:50][CH2:51]1)[C:44]([N:40]1[CH2:41][CH2:42][CH2:43][C@H:39]1[C:37]1[NH:38][C:34]([C:31]2[CH:32]=[CH:33][C:28]([C:23]3[CH:24]=[C:25]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C:15]3[NH:14][C:13]([C@@H:9]5[CH2:10][CH2:11][CH2:12][N:8]5[C:6](=[O:7])[C@@H:5]([NH:4][C:3](=[O:67])[O:2][CH3:1])[CH:64]([CH3:65])[CH3:66])=[N:17][CH:16]=3)[CH:27]=[CH:26]4)=[CH:29][CH:30]=2)=[CH:35][N:36]=1)=[O:63]

Participants

Conditions

Temperature: 0 °C

Procedure

To (S)-1-((S)-2-(5-(6-(4-(2-((S)-1-((S)-2-(benzyloxycarbonylamino)-2-(tetrahydro-2H-thiopyran-4-yl)acetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester (46 mg, 0.05 mmol) in ACN (0.4 mL) was add 33% HBr in HOAc (0.1 mL) and reaction mixture was cooled to 0° C. and then stirred for 2 hours. After concentrated to afford title compound as white solid (33 mg, 85%). MS (ESI) m/z 790 [M+H]+.

Workup

concentrationAfter concentrated

Sources & evidence

ORD record: ord-9474f80ffcad4e58927e24635662e0b4
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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