Ethyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate → HCID 66659888, compound

HRID 2391062Notes

Reaction equation

HRID 2391062 reaction equation
[CH:1]1([CH:4]([O:6][C:7](=[O:22])[NH:8][C:9]2[C:10]([CH3:21])=[N:11][O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH3:5])[CH2:3][CH2:2]1.[CH2:23]([O:25][C:26]([C:28]1([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)[CH2:30][CH2:29]1)=[O:27])[CH3:24]>>[CH2:23]([O:25][C:26]([C:28]1([C:31]2[CH:36]=[CH:35][C:34]([C:17]3[CH:18]=[CH:19][C:14]([C:13]4[O:12][N:11]=[C:10]([CH3:21])[C:9]=4[NH:8][C:7]([O:6][CH:4]([CH:1]4[CH2:3][CH2:2]4)[CH3:5])=[O:22])=[CH:15][CH:16]=3)=[CH:33][CH:32]=2)[CH2:29][CH2:30]1)=[O:27])[CH3:24]

Participants

3

Reactant 2

HCID 53217182Ethyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylateHCID 66660327HCID 66660327, compound

Product 1

HCID 66659888HCID 66659888, compound

Procedure

Prepared according to the procedure described in Example 1, Step 6 using [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-cyclopropyl-ethyl ester and 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester; the isolated material was then purified by preparative HPLC, using a Chiracel OD column (97:3 hexanes:EtOH) to provide enantiomer A and enantiomer B. Enantiomer A had a retention time of 27 minutes, enantiomer B had a retention time of 33 minutes.

Workup

  1. customPrepared
  2. customthe isolated material was then purified by preparative HPLC
  3. customto provide enantiomer A and enantiomer B

Sources & evidence

ORD record
ord-307a729df4364a3d82a019e40259763d
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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