1,2-Dichloroethane → HCID 53639334, compound

HRID 2187617Notes

Reaction equation

HRID 2187617 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:24][N:21]1[CH2:22][CH2:23][CH:18]([O:16][C:14](=[O:15])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH2:8])[CH2:19][CH2:20]1.[CH3:24][N:21]1[CH2:22][CH2:23][CH:18]([C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH2:10][CH2:11][S:12][CH3:13])[C:14]([O-:16])=[O:15])[CH2:19][CH2:20]1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 660484-Piperidinol, 1-methyl-HCID 89857Boc-L-methionine

Product 2

HCID 53639334HCID 53639334, compoundHCID 86758273HCID 86758273, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

L-methionine (N-methylpiperidin-4-yl) ester was prepared as follows: A solution of tert-butoxycarbonyl-L-methionine (5 g; 20 mmol), 4-hydroxy-1-methylpiperidine (3.3 g; 20 mmol); DMAP (2.44 g; 20 mmol) and EDC (4.6 g; 2.4 mmol) in dichloromethane (200 ml) was stirred at ambient temperature overnight. The mixture was extracted with dichloromethane. The organic phase was evaporated and purified by flash chromatography, eluting with dichloromethane/ethanol (97/3) to give 1-methylpiperidin-4-yl-2-tert-butoxycarbonylamino-4-methylsulfanylbutyrate. Yield 56%.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customThe organic phase was evaporated
  3. custompurified by flash chromatography
  4. washeluting with dichloromethane/ethanol (97/3)

Sources & evidence

ORD record
ord-abf79cb2fb024ec395ce96f37c855494
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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