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Diisopropylethylamine → N-(4-Benzyloxy-phenyl)-2-methanesulfonyl-acetamide

HRID 2238278
Notes
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Reaction equation

HRID 2238278 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][S:18]([CH2:21][C:22](O)=[O:23])(=[O:20])=[O:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:22](=[O:23])[CH2:21][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27238314-Benzyloxyaniline hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 37328412-Methanesulfonylacetic acid

Product 1

HCID 68481090N-(4-Benzyloxy-phenyl)-2-methanesulfonyl-acetamide

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), methanesulfonylacetic acid (2.35 g, 17.0 mmol) and HBTU (6.89 g, 18.2 mmol) in DMF (70 mL) was stirred at ambient temperature one minute. DIEA (6.5 mL, 37.2 mmol) was added all at once, and the resultant solution was stirred at ambient temperature. The solution was poured into water, and the product crystallized. The product, 5.4 g (99%), was collected by filtration and was used without any further purification in the subsequent reaction. MS m/z 320 (MH+). 1H NMR(DMSO-d6) δ 3.17 (s, 3H), 4.25 (s, 2H), 5.07 (s, 2H), 7.00 (d, 2H), 7.32-7.55 (m, 7H) and 10.32 (s, 1H).

Workup

  1. customthe product crystallized
  2. filtrationThe product, 5.4 g (99%), was collected by filtration
  3. customwas used without any further purification in the subsequent reaction

Sources & evidence

ORD record
ord-f967ee05982d47b2904ed7a809f186a8
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718692B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes