Dichloromethane → L-Lysine, N6-[(4-methoxyphenyl)diphenylmethyl]-

HRID 1767034Notes

Reaction equation

HRID 1767034 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:29]([OH:31])=[O:30])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=1.C(Cl)Cl.C(NCC)C>C(#N)C>[NH2:1][C@H:2]([C:29]([OH:31])=[O:30])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 11422318(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(((4-Methoxyphenyl)diphenylmethyl)amino)hexanoic acid2×

Product 1

HCID 10982650L-Lysine, N6-[(4-methoxyphenyl)diphenylmethyl]-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Fmoc-Lys(MMT) (9.7336 g) in 100 ml of mixture of methylene chloride and acetonitrile (1:1) at room temperature was added diethylamine (100 ml). The mixture was stirred at room temperature for 1.5 hrs. After removal of solvent, the residue was flushed with acetonitrile at 60° C. (90 ml×2), washed with acetonitrile (20 ml×3) and ether (20 ml×3). The solid was then dissolved as far as possible in 1:1 CH2Cl2/CH3OH (200 ml) and some solid byproduct was removed by filtering through filter paper. After removal of solvent and being dried in vacuo, 4.7707 g (82.2%, based on Fmoc-Lys) of pale yellow foam was obtained. ES(+)-MS: 147(Lys+1), 273(MMT).

Workup

  1. customAfter removal of solvent
  2. customthe residue was flushed with acetonitrile at 60° C. (90 ml×2)
  3. washwashed with acetonitrile (20 ml×3) and ether (20 ml×3)
  4. dissolutionThe solid was then dissolved as far as possible in 1:1 CH2Cl2/CH3OH (200 ml)
  5. customsome solid byproduct was removed
  6. filtrationby filtering
  7. filtrationthrough filter paper
  8. customAfter removal of solvent
  9. custombeing dried in vacuo, 4.7707 g (82.2%, based on Fmoc-Lys) of pale yellow foam
  10. customwas obtained

Sources & evidence

ORD record
ord-c279e0a4898543d5bbd2a51a60ad4054
Source dataset
uspto-grants-2007_06
Patent number
US07232805B2

Reaction notes

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