2-Aminopropanol → HCID 58770291, compound

HRID 2220289Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]3[S:22][C:21]([C:23]([OH:25])=O)=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:19]=3[CH:32]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:33][CH:34]([CH3:37])[CH2:35][OH:36]>>[OH:36][CH2:35][CH:34]([NH:33][C:23]([C:21]1[S:22][C:18]2[CH:17]=[CH:16][C:15]([NH:14][S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)(=[O:12])=[O:13])=[CH:32][C:19]=2[C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25])[CH3:37]

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 11989687HCID 11989687, compound

Product 1

HCID 58770291HCID 58770291, compoundYield 29%

Procedure

According to Step 1, after reaction of 5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzothiophene-2-carboxylic acid (155 mg, 0.33 mmol) with 2-amino-1-propanol (0.027 mL, 0.35 mmol) followed by chromatographic purification (silica gel, dichloromethane/methanol (0-10% methanol)) and recrystallization from ethyl acetate/hexane, the desired compound is obtained at 29% yield (51 mg).

Workup

customfollowed by chromatographic purification (silica gel, dichloromethane/methanol (0-10% methanol)) and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-0794906667fd46d7b37c5abe75c06e50
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417066B2

Reaction notes

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