Ammonia → HCID 53929760, compound

HRID 1358595Notes

Reaction equation

HRID 1358595 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.N.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH2:16]Cl>C1COCC1>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH2:16][N:6]1[CH:7]=[N:8][C:4]([CH2:3][C@@H:2]([C:9]([OH:11])=[O:10])[NH2:1])=[CH:5]1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 748322,6-Dichlorobenzyl chlorideHCID 178419078HCID 178419078, compound

Product 1

HCID 53929760HCID 53929760, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

L-histidine (3.13 g) was added to a solution of NaNH2 in liquid ammonia prepared from Na (0.93 g) and FeCl3 (catalytic amount) in liquid ammonia (50 ml) After 15 min., a solution of 2,6-dichlorobenzylchloride (3.96 g) in THF (5 ml) was added and the mixture was stirred for 3 hr. The reaction mixture was quenched with H2O and ether. The pH of the aqueous layer was adjusted to pH 8 with 5% HCl followed by cooling. The resulting precipitate was collected by filtration, washed with H2O, and dried to give 1-[(2,6-dichlorophenyl)methyl]-L-histidine (3.58 g). The obtained compound (0.80 g) was dissolved in MeOH (30 ml) and HCl gas was bubbled for 10 min. at 0° C. The reaction mixture was stirred for 15 hr. at room temperature and the solvent was removed in vacuo to give 1-[(2,6-Dichlorophenyl)methyl]-L-histidine methyl ester, dihydrochloride salt.

Workup

  1. customThe reaction mixture was quenched with H2O and ether
  2. temperatureby cooling
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-800876274c6d4abcbd6d84453c6c4570
Source dataset
uspto-grants-2003_07
Patent number
US06596752B1

Reaction notes

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