N-Benzyl-2-chloroacetamide → HCID 70061753, compound

HRID 2298260Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[CH2:32]([NH:39][C:40](=[O:43])[CH2:41]Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:41][C:40]([NH:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:43])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

Reactant 2

HCID 96233N-Benzyl-2-chloroacetamide

HCID 54334627HCID 54334627, compound

Product 1

HCID 70061753HCID 70061753, compound

Procedure

The title compound was prepared by alkylation of N-(toluene-4-sulfonyl)-L-prolyl-L-tyrosine methyl ester with N-benzyl-2-chloroacetamide (potasium carbonate, sodium iodide, refluxing butanone under Argon overnight). The product was purified by flash column chromatography (silica, 1:1 hexane:EtOAc) to afford the methyl ester as a white solid, mp 57-59° C.

Workup

customThe product was purified by flash column chromatography (silica, 1:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-11785d52ff4c4f928125b3284e26fce3
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492421B1

Reaction notes

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