Benzoic Acid → (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate

HRID 1776145Notes

Reaction equation

HRID 1776145 reaction equation
[NH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:8].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:57](O)(=[O:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C(Cl)Cl.O.C(OCC)(=O)C>[C:57]([NH:1][CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:8])(=[O:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60207723HCID 60207723, compound

Product 1

HCID 60207724(E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamateYield 65.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E)-tert-butyl 2-(6-aminohex-3-enamido)phenylcarbamate (100 mg, 0.3134 mmol), HATU (119.1 mg, 0.3134 mmol), DIEA (0.25 ml), benzoic acid (38 mg, 03134 mmol) in DCM was stirred at RT for 5 hours, The reaction mixture was poured onto 50 mL of ethyl acetate and 20 mL of water. The organic layers were washed with water (20 mL×3) and brine (3×20 mL), dried over Na2SO4 and concentrated to give the desired compound of (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate (86.16 mg, yield 65%) as a white solid after purification by column chromatography on silica gel (eluent: DCM:MeOH=200:1). LC-MS found 424 (M+H)+.

Workup

  1. washThe organic layers were washed with water (20 mL×3) and brine (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6fbd0d01aef24e2db58cc5e87d905868
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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