4-Methylmorpholine → HCID 59909748, compound

HRID 2183054Notes

Reaction equation

HRID 2183054 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][S:56]([CH2:59][CH2:60][CH3:61])(=[O:58])=[O:57]>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][S:56]([CH2:59][CH2:60][CH3:61])(=[O:58])=[O:57]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidHCID 22480845HCID 22480845, compound

Product 1

HCID 59909748HCID 59909748, compoundYield 98.8%

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), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (354 mg, 1.85 mmol), N-methylmorpholine (203 □1,1.85 mmol) and 1-hydroxybenzotriazole hydrate (227 mg, 1.67 mmol) in dichloromethane (20 ml) was treated with (1Z)-N′-hydroxy-2-(propylsulfonyl)ethanimidamide (300 mg, 1.67 mmol) and 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 solid (760 mg).

Workup

  1. stirringstirred for 20 minutes
  2. customThe layers were separated via a 5 micron
  3. filtrationfilter cartridge
  4. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf07f19ddd434570877566f5f720f471
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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