Phenylboronic Acid → Ethyl 3-[1,1'-biphenyl]-4-yl-2-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate

HRID 1058772Notes

Reaction equation

HRID 1058772 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:15][P:16]([OH:31])([CH:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:2]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:15][P:16]([OH:31])([CH:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 18668675Ethyl 3-(4-bromophenyl)-2-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate

Product 1

HCID 18668699Ethyl 3-[1,1'-biphenyl]-4-yl-2-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoateYield 97.6%

Procedure

The process is performed according to the operating conditions in 5.4., starting with 1.7 g (3.32 mmol) of ethyl 3-(4-bromophenyl)-2-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate and 4.05 g (3.32 mmol) of phenylboronic acid. 1.65 g of product are recovered (yield=97.6%).

Workup

  1. custom1.65 g of product are recovered (yield=97.6%)

Sources & evidence

ORD record
ord-3349035ee4a14cdcaeb3732661193bd0
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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