3-Methoxypropylamine → HCID 16493899, compound

HRID 1822770Notes

Reaction equation

HRID 1822770 reaction equation
ClC(OCC(C)C)=O.O.[C:10]([NH:17][C@H:18]([C:23]([OH:25])=O)[CH2:19][CH:20]([CH3:22])[CH3:21])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CN1CCOCC1.[CH3:33][O:34][CH2:35][CH2:36][CH2:37][NH2:38]>C1COCC1>[CH3:33][O:34][CH2:35][CH2:36][CH2:37][NH:38][C:23](=[O:25])[C@H:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[NH:17][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

Participants

6

Reactant 4

HCID 16723-MethoxypropylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 16493899HCID 16493899, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (520 μL, 4.0 mmol) was added to a solution of N-Boc leucine monohydrate (1.0 g, 4.0 mmol) and N-methyl morpholine (440 μL, 1.73 mmol) in THF at 0° C. After two minutes, 3-methoxypropylamine (410 μL, 4.0 mmol) was added and the mixture was allowed to warm to rt. After thirty minutes, the reaction mixture was filtered through a bed of celite and all volatiles were removed under reduced pressure to yield N-Boc-L-leucine-3-methoxypropyl amide (1.10 g, 92%) as a white solid. 1H NMR: (CDCl3) δ 0.93, 6H, d; 1.42, 9H, s; 3.35, 3H, s; 3.38, 2H, d; 3.43 m 2H, t; 4.03m 1H, m; 4.39, s, 1H; 4.91, 1H, m; 6.60, 1H, m,

Workup

  1. waitAfter thirty minutes
  2. filtrationthe reaction mixture was filtered through a bed of celite
  3. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-88ca1f7ec8cf4b0f88bcc26f11e1e80d
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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