Chloral → HCID 10944680, compound

HRID 594830Notes

Reaction equation

HRID 594830 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].[NH:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9](O)=[O:10]>CC#N>[Cl:4][C:3]([Cl:6])([Cl:5])[C@@H:2]1[N:7]2[CH2:14][CH2:13][CH2:12][C@H:8]2[C:9](=[O:10])[O:1]1

Participants

4

Reactant 2

HCID 6407ChloralHCID 145742L-Proline

Product 1

HCID 10944680HCID 10944680, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

22 ml (225 mmol, 2.5 eq) chloral was added to a suspension of 10.470 g (90.94 mmol, 1.0 eq) L-proline (102) in 45 ml MeCN at RT, and the obtained solution was stirred for 19.5 h at RT. The solvent was removed at reduced pressure and the residue dissolved and filtered in 100 ml DCM. The filtrate was concentrated, and this process was repeated three more times. 18.141 g (74.20 mmol, 82%) of the product 103 was obtained as a white solid.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue dissolved
  3. filtrationfiltered in 100 ml DCM
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eb37cd4b20b64a64825d2a42f1af26d3
Source dataset
uspto-grants-2016_01
Patent number
US09242985B2

Reaction notes

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