tert-Butyl bromoacetate → 2-[[1-(5-Cyanothiophene-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-(N-Cbz-7-aminonaphthalene-2-sulfonyl)amino]acetic acid tert-butyl ester

HRID 619848Notes

Reaction equation

HRID 619848 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][C:22]([NH:28][C:29]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[O:30])=[CH:23][CH:24]=4)[CH:19]=3)(=[O:17])=[O:16])[C:10]2=[O:39])[CH:4]=1)#[N:2].Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>>[C:45]([O:44][C:42](=[O:43])[CH2:41][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:39])[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][C:22]([NH:28][C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])=[O:16])([CH3:48])([CH3:47])[CH3:46]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 18392459N-Cbz-7-aminonaphthalene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide

Product 1

HCID 673651882-[[1-(5-Cyanothiophene-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-(N-Cbz-7-aminonaphthalene-2-sulfonyl)amino]acetic acid tert-butyl ester

Procedure

The title compound is prepared from N-Cbz-7-aminonaphthalene-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-8f61758b25f54bbd8163cd67c3ed2c4a
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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