Benzyl propionate → Indolizine-1,3-dicarboxylic acid 3-allyl ester 1-benzyl ester

HRID 1527195Notes

Reaction equation

HRID 1527195 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[N:19]2[C:14]([CH:15]=[CH:16][CH:17]=[CH:18]2)=[C:13](N=C=O)[CH:12]=1)=[O:10])[C:2]1[CH:7]=CC=CC=1.C(OC(=O)CBr)C=C.[CH2:31]([O:38][C:39](=[O:42])CC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([O:38][C:39]([C:13]1[CH:12]=[C:11]([C:9]([O:8][CH2:1][CH:2]=[CH2:7])=[O:10])[N:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[CH:18]2)=[O:42])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 31219Benzyl propionateHCID 527610Prop-2-enyl 2-bromoacetateHCID 866738121-Isocyanato-indolizine-3-carboxylic acid benzyl ester

Product 1

HCID 68283672Indolizine-1,3-dicarboxylic acid 3-allyl ester 1-benzyl ester

Procedure

The title compound was prepared using the protocol described in steps A and B for the preparation of 1-isocyanato-indolizine-3-carboxylic acid benzyl ester scheme A6 using bromo-acetic acid allyl ester in step A and propionic acid benzyl ester in step B. TLC, Rf (c-hexane/EtOAc 1:1)=0.8; MS (LC/MS): 336.1 [M+H]+, 358.1 [M+Na]+, 693.2 [2M+Na]+; tR (HPLC conditions a): 4.55 min.

Workup

  1. custom4.55 min.

Sources & evidence

ORD record
ord-9c9717122e8748bbace1fdd3a9ed42ae
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…