Hydrogen chloride-ethyl acetate → HCID 86755311, compound

HRID 1004158Notes

Reaction equation

HRID 1004158 reaction equation
C(OCC)(=O)C.[ClH:7].[OH:8][CH:9]([CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:10][N:11]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:37])[C@H:29]([C:31]2[N:32]=[C:33]([NH2:36])[S:34][CH:35]=2)[OH:30])=[CH:23][CH:22]=1)C(=O)OC(C)(C)C>>[ClH:7].[ClH:7].[OH:8][CH:9]([CH2:38][O:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:10][NH:11][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:37])[C@H:29]([C:31]2[N:32]=[C:33]([NH2:36])[S:34][CH:35]=2)[OH:30])=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 54306199HCID 54306199, compound

Product 1

HCID 86755311HCID 86755311, compound

Procedure

10 ml of a 4N hydrogen chloride-ethyl acetate solution was added to 10 ml of a methanolic solution of 285 mg of t-butyl (S)-N-(2-hydroxy-3-phenoxypropyl)-N-[2-[4-[[2-(2-aminothiazol-4-yl)-2-hydroxyacetyl]amino]phenyl]ethyl]-carbamate at room temperature. The reaction mixture was stirred at room temperature for four hours. The solvent was evaporated off and the residue was purified by means of silica gel column chromatography (eluate: chloroform/methanol=7/1) to obtain 222 mg of (S)-4'-[2-[(2-hydroxy-3-phenoxypropyl)-amino]ethyl]-2-(2-aminothiazol-4-yl)-2-hydroxyacetanilide dihydrochloride.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was purified by means of silica gel column chromatography (eluate: chloroform/methanol=7/1)

Sources & evidence

ORD record
ord-0c42d1f47f4f454c9c73717c149fa127
Source dataset
uspto-grants-2000_04
Patent number
US06048884

Reaction notes

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