Diisopropylethylamine → 4-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(2-nitro-benzenesulfonyl)-piperazin-2-one

HRID 1794962Notes

Reaction equation

HRID 1794962 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[NH:13][C:14](=[O:25])[C:15]2[N:16]=[CH:17][N:18]([CH2:21][C:22]([OH:24])=O)[C:19]=2[N:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][C:40]1=[O:45])(=[O:38])=[O:37])([O-:29])=[O:28].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[NH:13][C:14](=[O:25])[C:15]2[N:16]=[CH:17][N:18]([CH2:21][C:22]([N:42]3[CH2:43][CH2:44][N:39]([S:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[N+:27]([O-:29])=[O:28])(=[O:38])=[O:37])[C:40](=[O:45])[CH2:41]3)=[O:24])[C:19]=2[N:20]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 688024401-(2-Nitrobenzenesulfonyl)-piperazin-2-one HCl saltHCID 1354406332-[2-(Benzyloxycarbonylamino)-6-hydroxy-purin-9-yl]acetic acid

Product 1

HCID 1363776444-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(2-nitro-benzenesulfonyl)-piperazin-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-N-(benzyloxycarbonyl)-guanin-9-yl]-acetic acid (1.48 g, 4.5 mmol), 1-(2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (1.45 g, 4.5 mmol), and PyBOP (2.81 g, 5.4 mmol) in DMF (13 mL) was added N,N-diisopropylethylamine (1.96 mL, 13 mmol) at room temperature. After stirring for additional 40 min, the reaction mixture was diluted with water (80 mL) to precipitate solid. The solid was filtered off, washed with ethyl alcohol and triturated with acetonitrile and THF to give pure product (1.56 g, 58%). 1H NMR (DMSO-d6) δ 11.47 (s, 1H), 11.38 (s, 1H), 8.40˜7.96 (m, 4H), 7.82 (s, 0.6H), 7.78 (s, 0.4H), 7.45˜7.35 (m, 5H), 5.25 (s, 2H), 5.13 (s, 1.2H), 5.04 (s, 0.8H), 4.51 (s, 0.8H), 4.26 (s, 1.2H), 4.10˜4.02 (m, 2.4H), 3.93˜3.83 (m, 1.6H).

Workup

  1. customto precipitate solid
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl alcohol
  4. customtriturated with acetonitrile and THF

Sources & evidence

ORD record
ord-ffc349b066f24badb3f7d47f84bce57d
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

Loading…