3-Methoxypropylamine → HCID 131720195, compound

HRID 1378365Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].O.[C:8]([NH:15][C@H:16]([C:21]([OH:23])=O)[CH2:17][CH:18]([CH3:20])[CH3:19])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>>[C:8]([NH:15][C@H:16]([C:21]([CH2:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6])=[O:23])[CH2:17][CH:18]([CH3:19])[CH3:20])([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

Reactant 2

HCID 16723-Methoxypropylamine

HCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 131720195HCID 131720195, compound

Procedure

In substantially the same manner as Working Example 2, 3-methoxypropylamine (6.1 ml, Wako Pure Chemical Industries, Ltd.) was condensed with Boc-L-leucine monohydrate (5.00 g, manufactured by Peptide Institute, Inc.) to afford N-(Boc-L-leucyl)methoxypropylamine (17.5 g) as a colorless waxy product (yield 89%). The Boc group was deprotected by using TFA, and 1.21 g of the resultant compound was condensed, in substantially the same manner as Working Example 2, with (2S,3S)-ethyl hydrogen N-Z-aziridine-2,3-dicarboxylate (Compound 1, 1.93 g) to afford the above-titled compound (Compound 20; 2.55 g) as a white crystalline product (yield 89%).

Sources & evidence

ORD record: ord-5ee8d5fc549e4166ad0720919a51702f
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668128

Reaction notes

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