Diisopropylethylamine → (r)-5-(2-Acetamido-4-methylthiazol-5-yl)-n-(2-hydroxy-1-phenylethyl)furan-2-carboxamide

HRID 2386177Notes

Reaction equation

HRID 2386177 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[O:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:50]1[CH:55]=[CH:54][C:53]([C@H:56]([NH2:59])[CH2:57][OH:58])=[CH:52][CH:51]=1>>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[O:15][C:14]([C:16]([NH:59][C@H:56]([C:53]3[CH:54]=[CH:55][CH:50]=[CH:51][CH:52]=3)[CH2:57][OH:58])=[O:18])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 1347972-Amino-2-phenylethan-1-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 593622035-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

Product 1

HCID 59362159(r)-5-(2-Acetamido-4-methylthiazol-5-yl)-n-(2-hydroxy-1-phenylethyl)furan-2-carboxamide

Procedure

To 5 mL of the crude 4.49 millimolar solution of 5-(2-acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid was added 200 mg of TBTU and 1 mL of Hunig's base. To the stirred reaction mixture was then added 200 mg of S-phenylglycinol. The reaction was allowed to stir overnight and was then concentrated to dryness and dissolved in 1 mL of DMSO and filtered. The filtrate was purified via reverse phase chromatography to yield 4.1 mg of (R)-5-(2-acetamido-4-methylthiazol-5-yl)-N-(2-hydroxy-1-phenylethyl)furan-2-carboxamide as a white solid. LC/MS: 386.2 (M+H)/2.0 min.

Workup

  1. customTo the stirred reaction mixture
  2. concentrationwas then concentrated to dryness
  3. dissolutiondissolved in 1 mL of DMSO
  4. filtrationfiltered
  5. customThe filtrate was purified via reverse phase chromatography

Sources & evidence

ORD record
ord-544f287389c247bb8ea6224aeaec2582
Source dataset
uspto-grants-2012_09
Patent number
US08268818B2

Reaction notes

Loading…