tert-Butyl bromoacetate → 2-[[1-(5-Cyanothiophene-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-(N-Cbz-6-amino-5-chloronaphthalene-2-sulfonyl)amino]acetic acid tert-butyl ester

HRID 619850Notes

Reaction equation

HRID 619850 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][S:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([NH:29][C:30]([O:32][CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[O:31])[C:24]=4[Cl:28])[CH:19]=3)(=[O:17])=[O:16])[C:10]2=[O:40])[CH:4]=1)#[N:2].Br[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>>[C:46]([O:45][C:43](=[O:44])[CH2:42][N:14]([C@H:11]1[CH2:12][CH2:13][N:9]([CH2:8][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[S:7][CH:6]=2)[C:10]1=[O:40])[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:29][C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[C:24]=2[Cl:28])[CH:19]=1)(=[O:17])=[O:16])([CH3:49])([CH3:48])[CH3:47]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 18392457HCID 18392457, compound

Product 1

HCID 673652552-[[1-(5-Cyanothiophene-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-(N-Cbz-6-amino-5-chloronaphthalene-2-sulfonyl)amino]acetic acid tert-butyl ester

Procedure

The title compound is prepared from N-Cbz-6-amino-5-chloro-naphthalene-2-sulfonic acid-[1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide as described in EXAMPLE 141, Part D using tert-butyl bromoacetate in place of benzyl bromide. The crude product is purified by column chromatography eluting with a gradient of 5% EtOAc/CH2Cl2 to 10% EtOAc/CH2Cl2 to provide the title compound as a solid.

Workup

  1. customThe crude product is purified by column chromatography
  2. washeluting with a gradient of 5% EtOAc/CH2Cl2 to 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-6c2edee8080c4961920c98206afdc9ad
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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