Dicyclohexylcarbodiimide → Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrate

HRID 1003235Notes

Reaction equation

HRID 1003235 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:17]([S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])([CH3:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:17]([S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:33])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11816929Ethyl 4-(2-aminophenoxy)butanoateHCID 1879628012-[(Propan-2-yl)sulfanyl]dodecanoic acid

Product 1

HCID 18796054Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrateYield 45.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (4) (0.25 g, 1.14 mM) and (6) (0.274 g, 1.0 mM) in dry methylene chloride (10 mL) at room temperature was added 4-dimethylamino-pyridine (0.122 g, 1.0 mM) followed within one minute by a solution of N,N'-dicyclohexylcarbodiimide (0.22 g, 1.06 mM) in methylene chloride (1 mL), 3×1 mL rinses with methylene chloride. After 2 days, the filtered mixture was concentrated in vacuo and the residue flash chromatographed on silica gel using 15-20% ethyl acetate in hexane as eluant to give product 7 (0.22 g) as an oil that solidified readily in a short time.

Workup

  1. concentrationthe filtered mixture was concentrated in vacuo
  2. customthe residue flash chromatographed on silica gel using 15-20% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-b723848ac2504578b3ee1ff90119c83b
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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