1,2-Dichloroethane → HCID 89648258, compound

HRID 2281005Notes

Reaction equation

HRID 2281005 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([OH:30])=O)[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCCl.CCN(C(C)C)C(C)C.[C:44]1([NH2:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28](=[O:30])[NH:50][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])=[O:20])[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 81531DiisopropylethylamineHCID 89647708HCID 89647708, compound

Product 1

HCID 89648258HCID 89648258, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((((benzyloxy)carbonyl)amino)methyl)-1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidine-3-carboxylic acid (2462.00 mg; 5.64 mmol; 1.00 eq.) in DCE (4.0 ml) bis(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride (1435.59 mg; 5.64 mmol; 1.00 eq.) was added. After stirring for 15 mins at RT, DIEA (1.52 ml; 8.46 mmol; 1.50 eq.) and Phenylamine (525.18 mg; 5.64 mmol; 1.00 eq.) were added. The reaction mixture was stirred overnight at RT. The reaction mixture was added 50 ml of DCM, washed with brine, dried and concentrated. The residue was subjected to SNAP column (100 g) for purification, eluted with 20-50% EtOAc in hexane to yield the title compound (2600 mg, yield 90.1%)

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was subjected to SNAP column (100 g) for purification
  6. washeluted with 20-50% EtOAc in hexane

Sources & evidence

ORD record
ord-c530eb5618bf4859a9fe7771949787d9
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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