Tetrahydrofuran → HCID 178520232, compound

HRID 1611407Notes

Reaction equation

HRID 1611407 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([O:19][NH:20][C@H:21]([C:28]([OH:30])=[O:29])[CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1)=[O:18].O1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(Br)(Br)(Br)[Br:37]>>[Br:37][CH2:32][CH2:33][CH2:34][CH2:35][O:29][C:28](=[O:30])[C@H:21]([CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1)[NH:20][O:19][C:17](=[O:18])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 178520231HCID 178520231, compound

Product 1

HCID 178520232HCID 178520232, compound

Procedure

To a solution of [2-[(2,6-dichlorophenyl)amino]benzeneacetyloxy](L)-histidine (5 g, 11,54 mmoles) in tetrahydrofuran (100 ml) triphenylphosphine (9.08 g, 34.62 mmoles) and carbon tetrabromide (11.48 g, 34.62 mmoles) are added under stirring. The reaction mixture is left at room temperature for 24 hours, then the solvent is removed by evaporation at reduced pressure. The obtained crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 1/1. (S)-[2-[(2,6-dichlorophenyl)amino]benzeneacetyloxy](L)-histidine 4-bromobutyl ester is obtained.

Workup

  1. customthe solvent is removed by evaporation at reduced pressure
  2. customThe obtained crude product
  3. customis purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 1/1

Sources & evidence

ORD record
ord-c955c6316284407a86577faf8bde215e
Source dataset
uspto-grants-2006_01
Patent number
US06987120B1

Reaction notes

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