Triethylamine → HCID 68625716, compound

HRID 1819964Notes

Reaction equation

HRID 1819964 reaction equation
[CH2:1]([C:3]([C:21]1[S:25][C:24]([C:26](O)=[O:27])=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl.[CH3:31][O:32][C:33](=[O:36])[CH2:34][NH2:35].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>ClCCl>[CH3:31][O:32][C:33](=[O:36])[CH3:34].[CH2:1]([C:3]([C:21]1[S:25][C:24]([C:26]([NH2:35])=[O:27])=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10477025HCID 10477025, compound

Product 1

HCID 68625716HCID 68625716, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid (160 mg, 0.38 mmol), 2-amino-acetic acid methyl ester hydrochloride (53 mg, 0.42 mmol), EDCl (89 mg, 0.46 mmol) and triethylamine (0.134 ml, 0.96 mmol) in dichloromethane (5 ml) is stirred at RT overnight. The reaction is concentrated, partitioned between 1N HCl and EtOAc. The organic layer is concentrated and chromatographed (Hex to 30% EtOAc/Hex) to give the title compound (75 mg, 40%).

Workup

  1. concentrationThe reaction is concentrated
  2. custompartitioned between 1N HCl and EtOAc
  3. concentrationThe organic layer is concentrated
  4. customchromatographed (Hex to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-ab93351def3247b2a70e08d8bf5d31ea
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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