5-Hexyn-1-ol → N-{[(Hex-5-yn-1-yl)oxy]carbonyl}-3-methyl-L-valine

Reaction equation

[CH3:1][C:2]([CH3:17])([CH3:16])[C@@H:3]([C:13]([OH:15])=[O:14])[NH:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6].[CH2:18](O)CCCC#C>>[CH2:8]([O:7][C:5]([NH:4][C@H:3]([C:13]([OH:15])=[O:14])[C:2]([CH3:17])([CH3:16])[CH3:1])=[O:6])[CH2:9][CH2:10][CH2:11][C:12]#[CH:18]

Participants

Reactant 2

HCID 702345-Hexyn-1-ol

HCID 453799283-Methyl-N-{[(pent-4-en-1-yl)oxy]carbonyl}-L-valine

Product 1

HCID 57431194N-{[(Hex-5-yn-1-yl)oxy]carbonyl}-3-methyl-L-valine

Procedure

N-[(Hex-5-yn-1-yloxy)carbonyl]-3-methyl-L-valine was prepared according to the procedure for 3-methyl-N-[(pent-4-enyloxy)carbonyl]-L-valine by using hex-5-yn-1-ol instead of 4-pentenol. LRMS (ESI) m/z 256.2 [(M+H)+; calcd for C13H22NO4: 256.1].

Sources & evidence

ORD record: ord-e695c943672d4d929ea0c08e68fdf464
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470664B2

Reaction notes

Loading…