4-(2-(3-((Tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenylbromide → 4-(2-(3-((Tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenylboronic acid

HRID 735659Notes

Reaction equation

HRID 735659 reaction equation
C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.[C:29]([O:33][C:34]([NH:36][CH2:37][C:38]1[CH:39]=[C:40]([NH:44][C:45]([O:47][CH2:48][CH2:49][C:50]2[CH:55]=[CH:54][C:53](Br)=[CH:52][C:51]=2[Cl:57])=[O:46])[CH:41]=[CH:42][CH:43]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34]([NH:36][CH2:37][C:38]1[CH:39]=[C:40]([NH:44][C:45]([O:47][CH2:48][CH2:49][C:50]2[CH:55]=[CH:54][C:53]([B:25]([OH:27])[OH:26])=[CH:52][C:51]=2[Cl:57])=[O:46])[CH:41]=[CH:42][CH:43]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 578425534-(2-(3-((Tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenylbromideHCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

Product 1

HCID 578427284-(2-(3-((Tert-butoxycarbonylamino)methyl)phenylcarbamoyloxy)ethyl)-3-chlorophenylboronic acidYield 44%

Procedure

Using a procedure analogous to that used to prepare 6D, 61D (1.84 g, 3.8 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 61E (750 mg, 44%) as a solid. MS (ESI) m/z 447.1 (M−H)−.

Sources & evidence

ORD record
ord-6016366ce38143e691a0727c6210442c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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