Hydrochloric Acid → HCID 118292770, compound

HRID 1486900Notes

Reaction equation

HRID 1486900 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][C:8]1([CH2:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=2[CH2:20][CH2:21][C:22](O)=[O:23])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:34]1[CH2:39][CH2:38][S:37](=[O:41])(=[O:40])[CH2:36][CH2:35]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C>[O:40]=[S:37]1(=[O:41])[CH2:38][CH2:39][N:34]([C:22](=[O:23])[CH2:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=2[C:10]2[CH2:9][C:8]([CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:33])([CH2:25][C:26]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:32])[O:12][N:11]=2)[CH2:35][CH2:36]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6484228Thiomorpholine 1,1-dioxideHCID 118292738HCID 118292738, compound

Product 1

HCID 118292770HCID 118292770, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acid (317 mg), thiomorpholine 1,1-dioxide (92 mg), WSC (106 mg), HOBt (92 mg), and DMF (3 mL) was stirred at room temperature for 7 hours. To the reaction mixture, 0.1 M hydrochloric acid was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (140 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6a33f6213f5c4433b1ddf19e5822efe3
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

Loading…