Lithium Hydroxide → HCID 70212806, compound

HRID 383131Notes

Reaction equation

HRID 383131 reaction equation
Cl.[CH:2]1([CH2:8][NH:9][CH2:10][CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Li+].[OH-].[NH2:31][C@H:32]([C:37]([O:39][CH3:40])=[O:38])[CH2:33][CH2:34][S:35][CH3:36].Cl.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CO.CN(C=O)C.CCOC(C)=O>[CH3:40][O:39][C:37](=[O:38])[C@H:32]([CH2:33][CH2:34][S:35][CH3:36])[NH:31][C:16](=[O:17])[C:15]1[CH:20]=[CH:21][C:12]([CH2:11][CH2:10][NH:9][CH2:8][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:13][C:14]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28]

Participants

9

Reactant 5

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 66750451HCID 66750451, compound

Product 1

HCID 70212806HCID 70212806, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-(N-(cyclohexylmethyl)aminoethyl)-2-(2-methylphenyl)benzoate hydrochloride (1.33 g, 3.31 mmol) was treated with sat. LiOH (1.3 mL, 6.95 mmol) in 50 mL methanol at 60° C. until no starting material remained by tlc. The solution was evaporated to dryness and treated with Met-OMe.HCl (0.99 g, 4.96 mmol), EDAC (1.26 g, 6.6 mmol), HOBt (1.5 g, 9.9 mmol), and TEA (to pH 6˜7) in 25 mL DMF. Standard aqueous workup followed by flash chromatography (100% EtOAc) provided 1.5 g of the title compound. MS m/e 497 (M−H)−.

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-bc87e74029594217aa83c912a6d68277
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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