3-Fluoroaniline → HCID 89647587, compound

HRID 2281009Notes

Reaction equation

HRID 2281009 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH:13][C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH:10]([C:23](O)=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.CCN(C(C)C)C(C)C.[F:50][C:51]1[CH:52]=[C:53]([NH2:57])[CH:54]=[CH:55][CH:56]=1>ClCCCl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH:13][C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:22])[CH3:21])=[O:15])[CH:10]([C:23](=[O:24])[NH:57][C:53]2[CH:54]=[CH:55][CH:56]=[C:51]([F:50])[CH:52]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 97423-FluoroanilineHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 68714710HCID 68714710, compound

Product 1

HCID 89647587HCID 89647587, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-trimethylsilanyl-ethoxycarbonylamino)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (3200.00 mg; 8.54 mmol; 1.00 eq.) in DCE (40.0 ml), bis(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride (2392.68 mg; 9.40 mmol; 1.10 eq.) was added. After stirring for 15 mins. DIEA (1.69 ml; 9.40 mmol; 1.10 eq.) and 3-fluoro-phenylamine (1044.40 mg; 9.40 mmol; 1.10 eq) were added. The reaction mixture was stirred overnight at 45° C. The reaction solution was diluted with EtOAc, washed, dried and concentrated to give the crude product, which was subjected for SNAP (100 g) column for purification (eluted with 20-50% EtOAc in hexane) to afford the title compound (1700 mg, 42.5%).

Workup

  1. stirringThe reaction mixture was stirred overnight at 45° C
  2. washwashed
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas subjected for SNAP (100 g) column for purification (eluted with 20-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-62022ddb454d4850a549f475cee94fec
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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