Propionic Acid → 5-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid propionyl-amide

HRID 1819953Notes

Reaction equation

HRID 1819953 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[S:21][C:20]([S:22]([NH2:25])(=[O:24])=[O:23])=[C:19]([CH3:26])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:27].CCN=C=NCCCN(C)C.[C:42](O)(=[O:45])[CH2:43][CH3:44]>CN(C1C=CN=CC=1)C.ClCCl>[C:42]([NH:25][S:22]([C:20]1[S:21][C:17]([C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:28])[C:2]([CH3:1])([CH3:29])[CH3:30])=[C:7]([CH3:27])[CH:8]=2)([CH2:13][CH3:14])[CH2:15][CH3:16])=[CH:18][C:19]=1[CH3:26])(=[O:24])=[O:23])(=[O:45])[CH2:43][CH3:44]

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57890063HCID 57890063, compound

Product 1

HCID 117559705-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid propionyl-amideYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid amide (330 mg, 0.73 mmol), EDCI (210 mg, 1.1 mmol), propionic acid (82 μL, 1.1 mmol) and DMAP (50 mg) in dichloromethane (10 ml) is stirrred overnight. The reaction is diluted with dichloromethane and washed with 1N HCl. The organic phase is concentrated and chromatographed (Hex to 30% EtOAc/Hex) to give the title compound (92%).

Workup

  1. washwashed with 1N HCl
  2. concentrationThe organic phase is concentrated
  3. customchromatographed (Hex to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-3a2cb4d1a41646ec8a6ac3bad31d9ab3
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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