Potassium Carbonate → HCID 86757776, compound

HRID 1699409Notes

Reaction equation

[OH:1][C@H:2]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:3][N:4]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:28])[CH2:22][C:23]2[NH:24][CH:25]=[CH:26][N:27]=2)=[CH:16][CH:15]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].[F:41][C:42]1[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=1[CH2:44]Br>C(#N)C>[F:41][C:42]1[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=1[CH2:44][N:24]1[CH:25]=[CH:26][N:27]=[C:23]1[CH2:22][C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][N:4]([CH2:3][C@H:2]([OH:1])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[CH:15][CH:16]=1)=[O:28]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 403 mg of tert-butyl (R)-N-(2-hydroxy-2-phenylethyl)-N-[2-[4-[(2-1H-imidazol-2-ylacetyl)amino]phenyl]ethyl]carbamate in 10 ml of acetonitrile were added 120 mg of potassium carbonate and 164 mg of 2-fluorobenzyl bromide successively at room temperature. The reaction solution was stirred at 50° C. for 12 hours. Insoluble matters were filtered off using Celite, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to give 253 mg of tert-butyl (R)-N-[2-[4-[[2-[1-(2-fluorobenzyl)-1H-imidazol-2-yl]-acetyl]amino]phenyl]ethyl]-N-(2-hydroxy-2-phenylethyl)-carbamate.

Workup

filtrationInsoluble matters were filtered off
customthe solvent was evaporated
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-4c675ac2794b4f77974668b547acffbb
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346532B1

Reaction notes

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