Aniline → HCID 89647803, compound

HRID 2281007Notes

Reaction equation

HRID 2281007 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])([C:13]([OH:15])=O)[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.[C:52]1([NH2:58])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])([C:13](=[O:15])[NH:58][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 89647553HCID 89647553, compound

Product 1

HCID 89647803HCID 89647803, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzyloxycarbonylamino-methyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (2200.00 mg; 5.81 mmol; 1.00 eq.) in DCE (40.0 ml), bis(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride (1627.95 mg; 6.40 mmol; 1.10 eq.) was added. After stirring for 15 mins. DIEA (1.25 ml; 6.98 mmol; 1.20 eq.) and phenylamine (595.55 mg; 6.40 mmol; 1.10 eq) were added. The reaction mixture was stirred overnight at RT. DCM (100 ml) was added. The solution was washed with brine, dried and concentrated to give the crude product, which was subjected for biotage for purification (20-50% EtOAc in hexane) to afford the title compound (1800 mg, 68.3%).

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. washThe solution was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas subjected for biotage for purification (20-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-afb801ea953244b7851591a5e2d4a23e
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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