Acetic Acid → 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzoyloxymethyl ester dihydrochloride salt

HRID 1384507Notes

Reaction equation

HRID 1384507 reaction equation
[CH:1]([C:3]1[CH:52]=[CH:51][C:6]([C:7]([O:9][CH2:10][O:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][C:24]([NH:37][C:38]([O:40][CH2:41][C:42]3[O:43][C:44]4[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=4[CH:46]=3)=[O:39])([C:26](=[O:36])[NH:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])[CH3:25])=[CH:15]2)=[O:13])=[O:8])=[CH:5][CH:4]=1)=O.[OH:53][CH2:54][CH2:55][N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1.C(O)(=O)C.C(Cl)(Cl)[Cl:67]>>[ClH:67].[ClH:67].[OH:53][CH2:54][CH2:55][N:56]1[CH2:61][CH2:60][N:59]([CH2:1][C:3]2[CH:52]=[CH:51][C:6]([C:7]([O:9][CH2:10][O:11][C:12]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]([CH2:23][C:24]([NH:37][C:38]([O:40][CH2:41][C:42]4[O:43][C:44]5[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=5[CH:46]=4)=[O:39])([C:26](=[O:36])[NH:27][CH:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH3:29])[CH3:25])=[CH:15]3)=[O:13])=[O:8])=[CH:5][CH:4]=2)[CH2:58][CH2:57]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 76771-(2-Hydroxyethyl)piperazineHCID 206699173-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester

Product 1

HCID 702064963-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzoyloxymethyl ester dihydrochloride saltYield 69%

Procedure

NaHB(OAc)3 (0.423 g, 1.996 mmol, 1.4 eq.) was added in three equal portions in 10 minutes to a cloudy solution of compound 19 (1.0 g, 1.43 mmol), N-hydroxyethylpiperazine (0.192 mL, 1.57 mmol, 1.1 eq.) and acetic acid (0.179 mL, 3.14 mmol, 2.2 eq.) in dry chloroform (20 mL) under N2 in an ice bath. The reaction was stirred in ice bath for 30 minutes and at room temperature overnight to give a white suspension. The reaction was worked up as above to give compound 20d as a white foam (0.804 g, 69%).

Workup

  1. customat room temperature overnight to give a white suspension

Sources & evidence

ORD record
ord-285e65663e2d497d8e340bde34aede3d
Source dataset
uspto-grants-2001_07
Patent number
US06258800B1

Reaction notes

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