Diisopropylethylamine → (E)-tert-butyl2-(6-(tert-butyldimethylsilyloxy)hex-3-enamido)phenylcarbamate

HRID 1776141Notes

Reaction equation

HRID 1776141 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].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.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61]>C(Cl)Cl.O.C(OCC)(=O)C>[C:60]([O:59][C:58](=[O:64])[NH:57][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=1[NH:50][C:14](=[O:16])[CH2:13]/[CH:12]=[CH:11]/[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])([CH3:63])([CH3:61])[CH3:62]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60207716(E)-6-(tert-butyldimethylsilyloxy)hex-2-enoic acid

Product 1

HCID 70230367(E)-tert-butyl2-(6-(tert-butyldimethylsilyloxy)hex-3-enamido)phenylcarbamateYield 61.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E)-6-(tert-butyldimethylsilyloxy)hex-2-enoic acid (12.0 g, 49.2 mmol), HATU (18.69 g, 49.2 mmol), DIEA (30 mL), tert-butyl 2-aminophenylcarbamate (2) (10.23 g, 49.2 mmol) in DCM was stirred at RT for 5 hours, The reaction mixture was poured onto 500 mL of ethyl acetate and 200 mL of water, the organic layer was washed with water (250 mL×3) and brine (3×200 mL), dried over Na2SO4 and concentrated to give the desired compound of (E)-tert-butyl2-(6-(tert-butyldimethylsilyloxy)hex-3-enamido)phenylcarbamate (13.1 g, 44%) as a yellow oil after purification by column chromatography on silica gel (eluent: PE:EA=8:1). LC-MC (M+1) 435 (M+H)+

Workup

  1. washthe organic layer was washed with water (250 mL×3) and brine (3×200 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5664bfbedc9f4044a8e296af8e00dc17
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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