Triethylamine → 2-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acid methyl ester

HRID 736521Notes

Reaction equation

HRID 736521 reaction equation
[CH2:1]([C:3]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[C:23]([CH3:30])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl.[CH3:32][O:33][C:34](=[O:39])[C:35]([NH2:38])([CH3:37])[CH3:36].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>>[CH3:32][O:33][C:34](=[O:39])[C:35]([NH:38][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([C:3]([CH2:1][CH3:2])([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])=[C:8]([CH3:20])[CH:7]=2)[CH2:4][CH3:5])=[CH:22][C:23]=1[CH3:30])([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 578493484-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid

Product 1

HCID 578493282-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acid methyl esterYield 77.4%

Procedure

4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid (437 mg, 1.07 mmol), α-aminoisobutyric acid methyl ester hydrochloride (247 mg, 1.61 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (309 mg, 1.61 mmol), 1-hydroxybenzotriazole hydrate (218 mg, 1.61 mmol) and triethylamine (597 μL, 4.28 mmol) are reacted and purified analogous to Example 1J to give the title compound (419 mg, 77%).

Workup

  1. custompurified analogous to Example 1J

Sources & evidence

ORD record
ord-2c6a249e4d5b411da12c7b59d8ff0fc1
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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