(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → (1-(7-(2-Cyanobenzyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

HRID 458624Notes

Reaction equation

HRID 458624 reaction equation
Cl[C:2]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]#[N:15])[C:9]2[C:8](=[O:20])[N:7]([CH3:21])[C:6](=[O:22])[N:5]([CH3:23])[C:4]=2[N:3]=1.[C:24]([O:28][C:29]([NH:31][C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([O:28][C:29](=[O:30])[NH:31][CH:32]1[CH2:36][CH2:35][N:34]([C:2]2[N:10]([CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])[C:9]3[C:8](=[O:20])[N:7]([CH3:21])[C:6](=[O:22])[N:5]([CH3:23])[C:4]=3[N:3]=2)[CH2:33]1)([CH3:27])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 88509802-(8-Chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

Product 1

HCID 69136322(1-(7-(2-Cyanobenzyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

Procedure

2-(8-Chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile (1 A) (100 mg, 0.30 mmol) was reacted with (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (282 mg, 1.52 mmol), and purified as described in example 7, step A, to afford compound (8A) as white crystals.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-39befd777f0542b6945a2c9ca6810a17
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

Loading…