Acetic Acid → 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-{[bis-(2-hydroxy-ethyl)-amino]-methyl}-benzoyloxymethyl ester monohydrochloride salt

HRID 1384510Notes

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][NH:56][CH2:57][CH2:58][OH:59].C(O)(=O)C.[Cl:64]CCl>>[ClH:64].[OH:53][CH2:54][CH2:55][N:56]([CH2:1][C:3]1[CH:4]=[CH:5][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:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH3:29])[CH3:25])=[CH:15]2)=[O:13])=[O:8])=[CH:51][CH:52]=1)[CH2:57][CH2:58][OH:59]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 6344Dichloromethane

HCID 8113Diethanolamine

HCID 206699173-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester

Product 1

HCID 702070673-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-{[bis-(2-hydroxy-ethyl)-amino]-methyl}-benzoyloxymethyl ester monohydrochloride saltYield 42%

Procedure

NaHB(OAc)3 (0.212 g, 1.0 mmol, 1.4 eq.) was added in three equal portions in 10 minutes to a cloudy solution of compound 19 (0.5 g, 0.713 mmol), bis(2-hydroxyethyl)amine (0.15 g, 1.43 mmol, 2.0 eq.) and acetic acid (0.04 mL, 0.71 mmol, 1.0 eq.) in dry dichloromethane (15 mL) under N2 in an ice bath. The reaction was stirred in ice bath for 30 minutes and room temperature for 40 hours to give a white suspension. The reaction was worked up and purified as above to give compound 20g (0.24 g, 42%) as a white foam.

Workup

customroom temperature for 40 hours to give a white suspension
custompurified as above

Sources & evidence

ORD record: ord-7c52fa6c87d24c7cb455f3feaaeeb79a
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258800B1

Reaction notes

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