Diisopropylamine → methyl 4'-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylate

HRID 2220436Notes

Reaction equation

[NH2:1][C@@H:2]([CH3:12])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4].C(NC(C)C)(C)C.Br[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[C:32]([S:40][CH:41]([CH3:43])[CH3:42])[CH:31]=2)=[CH:26][CH:25]=1>CN(C)C=O.C(OCC)(=O)C>[OH:4][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[C@@H:2]([NH:1][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[C:32]([S:40][CH:41]([CH3:42])[CH3:43])[CH:31]=2)=[CH:28][CH:29]=1)[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[(1R,2S)-2-amino-1-hydroxypropyl]-phenol (75.4 mg) in N,N-dimethylformamide (1 ml) were added diisopropylamine (72.9 μl) and methyl 4′-(2-bromoethoxy)-3-(isopropylthio)-4-biphenylcarboxylate (142 mg) in N,N-dimethylformamide (0.4 ml) at room temperature and stirred at 100° C. for 4 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution, water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography to give methyl 4′-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylate (113 mg).

Workup

washwashed with saturated sodium bicarbonate aqueous solution, water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record: ord-d74e48ea67ef40389ad1206cc63405dc
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417060B2

Reaction notes

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