Hydrochloric Acid → N-{[2-(2,6-dichlorophenyl-amino)-phenyl]-acetyl}-L-leucyl-L-serine

HRID 904859Notes

Reaction equation

HRID 904859 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26]C1C=CC([N+]([O-])=O)=CC=1)=O.Cl.[NH2:37][C@H:38]([C:43]([NH:45][C@H:46]([C:49]([OH:51])=[O:50])[CH2:47][OH:48])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41]>CN(C)C=O>[Cl:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[C:10]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:49]([OH:51])=[O:50])[CH2:47][OH:48])=[O:44])[CH2:39][CH:40]([CH3:41])[CH3:42])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 6992130Leu-SerHCID 203870824-Nitrophenyl 2-(2,6-dichlorophenyl-amino)-phenyl-acetate

Product 1

HCID 53916881N-{[2-(2,6-dichlorophenyl-amino)-phenyl]-acetyl}-L-leucyl-L-serine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 ml of triethylamine are added to a solution of 4.2 g of 4-nitrophenyl 2-(2,6-dichlorophenyl-amino)-phenyl-acetate and 3.6 g of the hydrochloride of the methyl ester of L-leucyl-L-serine in 30 ml of dimethylformamide and the mixture is allowed to react for one hour at room temperature. It is then acidified to pH 5 with 1 N hydrochloric acid and partitioned between chloroform and water. After washing with water, the organic phase is dried and evaporated. The residue is ground with diethyl ether. After recrystallising from a mixture of ethyl acetate and petroleum ether, the methyl ester of N-{[2-(2,6-dichlorophenyl-amino)-phenyl]-acetyl}-L-leucyl-L -serine is obtained as colourless crystals; melting point 216°-218°: [α]D 32 -30° (c=0.635 in chloroform).

Workup

  1. customto react for one hour at room temperature
  2. custompartitioned between chloroform and water
  3. washAfter washing with water
  4. customthe organic phase is dried
  5. customevaporated
  6. customAfter recrystallising from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-f473cc09adda49b4951dd578bf007d63
Source dataset
uspto-grants-1983_12
Patent number
US04420490

Reaction notes

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