3-Iodo-1-propanol → N-(3,5-Difluorophenylacetyl)-L-alaninyl-L-phenylalanine 3-Iodopropyl Ester

HRID 636174

Reaction equation

HRID 636174 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:26]([OH:28])=[O:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[I:29][CH2:30][CH2:31][CH2:32]O>CO.C(Cl)Cl>[I:29][CH2:30][CH2:31][CH2:32][O:27][C:26](=[O:28])[C@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:17][C:15](=[O:16])[C@H:13]([CH3:14])[NH:12][C:10](=[O:11])[CH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

4

Reactant 2

HCID 693903-Iodo-1-propanolHCID 22895006N-(N-(3,5-difluorophenylacetyl)-L-alaninyl]-L-phenylalanine

Product 1

HCID 9807836N-(3,5-Difluorophenylacetyl)-L-alaninyl-L-phenylalanine 3-Iodopropyl Ester

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following General Procedure B and using N-[N-(3,5-difluorophenylacetyl)-L-alaninyl]-L-phenylalanine (prepared by coupling N-(3,5-difluorophenylacetyl)-L-alanine (from Example B2 above) and L-phenylalanine (Aldrich) using General Procedure B) and 3-iodo-1-propanol (Aldrich), the title compound was prepared as a solid. The reaction was monitored by tlc (Rf=0.45 in 5% MeOH/methylene chloride) and the product was purified by preparative tlc using 5% MeOH/methylene chloride.

Workup

  1. customthe product was purified by preparative tlc

Sources & evidence

ORD record
ord-3af6f5e270594dfbb167cc84ed3c3dc4
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Linked notes

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