4-(Benzylcarbamoyl)benzeneboronic acid → 1-Methylethyl 4-{[(4'-{[(phenylmethyl)amino]carbonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylate

HRID 423465Notes

Reaction equation

HRID 423465 reaction equation
[C:1]1([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]2)=[CH:23][CH:22]=1>>[C:1]1([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH:29]4[CH2:30][CH2:31][N:32]([C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH2:33][CH2:34]4)=[CH:25][CH:26]=3)=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 27732434-(Benzylcarbamoyl)benzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591778121-Methylethyl 4-{[(4'-{[(phenylmethyl)amino]carbonyl}-4-biphenylyl)oxy]methyl}-1-piperidinecarboxylateYield 15%

Procedure

The title compound (7.1 mg, 15%) was prepared from (4-{[(phenylmethyl)amino]carbonyl}phenyl)boronic acid (25.5 mg, 0.1 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (Example 9, Step 2, 36 mg, 0.10 mmol) in a manner similar to Example 9, Step 3. LRMS (ESI), m/z 487 (M+H).

Sources & evidence

ORD record
ord-600d89ab76a14d29a634d6bc8d37ea2a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…