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Diisopropylethylamine → HCID 67432873, compound

HRID 1040015
Notes
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Reaction equation

HRID 1040015 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)=[O:5].[Si:15]([O:32][CH2:33][C:34]([CH3:39])([CH3:38])[C:35](O)=[O:36])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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>CN(C=O)C.C(OCC)(=O)C>[Si:15]([O:32][CH2:33][C:34]([CH3:39])([CH3:38])[C:35]([NH:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)=[O:5])=[O:36])([C:28]([CH3:30])([CH3:31])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27743743-Nitrophenacylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160671723-((Tert-butyl(diphenyl)silyl)oxy)-2,2-dimethylpropanoic acid

Product 1

HCID 67432873
HCID 67432873, compound
Yield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-1-(3-nitrophenyl)ethanone HCl salt (300 mg, 138 mmol) and 3-{[tert-butyl(diphenyl)silyl]oxy}-2,2-dimethylpropanoic acid (543 mg, 1.52 mmol) in DMF (1.3 mL) was added HATU (579 mg, 1.52 mmol) and the mixture was cooled to 0° C. Hunig's base (726 μL, 4.15 mmol) was added, and the mixture was stirred for two hours at this temperature. The mixture was diluted with ethyl acetate (30 mL), then washed with 1:1 water:saturated NaHCO3(aq) (30 mL) and 1:1 water:brine (2×30 mL). The aqueous fractions were further extracted with ethyl acetate (30 mL), then the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Purification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate) provided 680 mg of 3-{[tert-butyl(diphenyl)silyl]oxy}-2,2-dimethyl-N-[2-(3-nitrophenyl)-2-oxoethyl]propanamide (1.31 mmol, 95%) as a white solid.

Workup

  1. washwashed with 1:1 water
  2. extractionThe aqueous fractions were further extracted with ethyl acetate (30 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica gel (100:0 to 50:50, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-1c9cea743bc24d21ba31f234143ddaf6
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes