Propargyl bromide → 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(prop-2-yn-1-yl)-1,1,2(R)-pentanetricarboxylate

HRID 1464359Notes

Reaction equation

HRID 1464359 reaction equation
[CH3:1][CH:2]([CH3:33])[CH2:3][C@@H:4]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH2:34](Br)[C:35]#[CH:36]>>[CH3:1][CH:2]([CH3:33])[CH2:3][C@@H:4]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C:5]([CH2:36][C:35]#[CH:34])([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

3

Reactant 2

HCID 7842Propargyl bromideHCID 18660804Dibenzyl 3(RS)-tert-butoxycarbonyl-2(R)-isobutylsuccinate

Product 1

HCID 867477771,2-dibenzyl 1-tert.butyl 4-methyl-1-(prop-2-yn-1-yl)-1,1,2(R)-pentanetricarboxylateYield 103%

Procedure

In a manner analogous to that described in Example 45(i), from 5.0 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1,1,2(R)-pentanetricarboxylate and 3.3 g of propargyl bromide there were obtained 5.58 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(prop-2-yn-1-yl)-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil; MS 493 (M+H)+.

Sources & evidence

ORD record
ord-a8860720486748e292b9c70107fed8ba
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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