4-Ethoxycarbonylphenylboronic acid → HCID 50943869, compound

HRID 2275748Notes

Reaction equation

C(O[C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=O)C.[NH2:15][C:16]1[CH2:17][C:18]([C:28]([N:30]([CH2:34][C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][CH3:33])=[O:29])=[CH:19][C:20]2[CH:26]=[CH:25][C:24](Br)=[CH:23][C:21]=2[N:22]=1.BrC1C=CC2=C(C=1)N=C(N[C:67](=[O:73])[O:68][C:69]([CH3:72])([CH3:71])[CH3:70])CC(C(=O)N(CCCO[Si](C(C)(C)C)(C)C)CCC)=C2>>[NH2:15][C:16]1[CH2:17][C:18]([C:28](=[O:29])[N:30]([CH2:34][C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][CH3:33])=[CH:19][C:20]2[CH:26]=[CH:25][C:24]([C:9]3[CH:8]=[CH:7][C:6]([CH2:4][C:67]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:73])=[CH:11][CH:10]=3)=[CH:23][C:21]=2[N:22]=1

Participants

Reactant 3

HCID 27343504-Ethoxycarbonylphenylboronic acid

HCID 67087501HCID 67087501, compound

HCID 86652684tert-butyl (1E,4E)-8-bromo-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-2-ylcarbamate

Product 1

HCID 50943869HCID 50943869, compoundYield 32%

Procedure

tert-Butyl 2-(4-((1E,4E)-2-amino-4-((2-amino-2-oxoethyl)(propyl)carbamoyl)-3H-benzo[b]azepin-8-yl)phenyl)acetate (32%) was prepared as described below in Steps 1 and 2, except for substituting isobutyl tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate for 4-(ethoxycarbonyl)phenylboronic acid and (1E,4E)-2-amino-N-(2-amino-2-oxoethyl)-8-bromo-N-propyl-3H-benzo[b]azepine-4-carboxamide for tert-butyl (1E,4E)-8-bromo-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-2-ylcarbamate.

Sources & evidence

ORD record: ord-ed19cb1a1a9a41fb82dc9bd6f04b9d58
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126940B2

Reaction notes

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