4-Methylmorpholine → 1-O-[(Z)-(1-amino-2-pyridin-4-ylethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate

HRID 2183063Notes

Reaction equation

HRID 2183063 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.O/[N:53]=[C:54](\[NH2:62])/[CH2:55][C:56]1[CH:61]=[CH:60][N:59]=[CH:58][CH:57]=1>ClCCl.O>[NH2:62]/[C:54](=[N:53]\[O:10][C:9]([C@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])=[O:11])/[CH2:55][C:56]1[CH:61]=[CH:60][N:59]=[CH:58][CH:57]=1

Participants

8

Reactant 5

HCID 79724-Methylmorpholine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidHCID 24688407N'-hydroxy-2-pyridin-4-ylethanimidamide

Product 1

HCID 167490061-O-[(Z)-(1-amino-2-pyridin-4-ylethylidene)amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioateYield 116.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-(2-tert-butoxy-2-oxoethyl)-5-cyclohexylpentanoic acid (Preparation 1) (500 mg, 1.67 mmol) in dichloromethane (20 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (354 mg, 1.85 mmol), N-methylmorpholine (203 μl, 1.85 mmol) and 1-hydroxybenzotriazole hydrate (227 mg, 1.67 mmol). (1Z)-N′-hydroxy-2-(4-pyridinyl)ethanimidamide (WO 9600720) (374 mg, 1.67 mmol) followed by N-methylmorpholine (369 μl, 3.34 mmol) were added to the reaction mixture which was stirred at room temperature for 18 hours. The reaction mixture was diluted with water (10 ml) and stirred for 20 minutes. The layers were separated via a 5 micron filter cartridge. The organic solvent was removed under reduced pressure to afford the title compound as a yellow oil (840 mg). This was used without further purification in the following step.

Workup

  1. additionwere added to the reaction mixture which
  2. stirringstirred for 20 minutes
  3. customThe layers were separated via a 5 micron
  4. filtrationfilter cartridge
  5. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-80dea7f7c8e7444b96635a6b2283b6ac
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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