Hexachloroethane → METHYL N-BOC-3-CHLORO-L-ALANINATE

HRID 714142Notes

Reaction equation

HRID 714142 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20]C(Cl)(Cl)C(Cl)(Cl)Cl.[C:28]([O:32][C:33]([NH:35][C@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:37]O)=[O:34])([CH3:31])([CH3:30])[CH3:29]>ClCCCl.ClCCCl.ClCCCl.C(Cl)Cl>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:39]([O:41][CH3:42])=[O:40])[CH2:37][Cl:20])=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 12182794METHYL N-BOC-3-CHLORO-L-ALANINATEYield 61.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 87695156HCID 87695156, compoundSolvent

Procedure

A solution of triphenylphosphine (4.55 g, 17.4 mmol) and hexachloroethane (3.9 g, 16.5 mmol) in 1,2-dichloroethane (18 mL) prepared at 0° C. was added via cannula into a flask containing a solution of methyl N-(tert-butoxycarbonyl)-L-serinate (3.2 g, 14.6 mmol) in 1,2-dichloroethane DCE (40 mL), kept at 0° C. under N2 atmosphere. After the addition was completed, the reaction mixture was further stirred at room temperature for 2 h, diluted with DCM, washed with sat NaHCO3, dried over MgSO4, filtered and concentrated. Purification made through chromatographic column of silicagel eluted with 10% to 50% EtOAc in hexane for 30 min, to afford 2.13 g (61% yield) of title compound as white crystals. MS: m/z=260.0 (MNa+).

Workup

  1. additionwas added via cannula into a flask
  2. customkept at 0° C. under N2 atmosphere
  3. additionAfter the addition
  4. washwashed
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washof silicagel eluted with 10% to 50% EtOAc in hexane for 30 min

Sources & evidence

ORD record
ord-632dce4151594184ab5a458779f8e933
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

Loading…