Isoamylamine → HCID 10040487, compound

HRID 1378363Notes

Reaction equation

[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].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]([NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])=[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 7894Isoamylamine

HCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 10040487HCID 10040487, compound

Procedure

In substantially the same manner as working Example 2, isopentylamine (2.33 ml) was condensed with Boc-L-leucine monohydrate (5.00 g, manufactured by Peptide Institute, Inc.) to give N-(Boc-L-leucyl)isopentylamine (5.73 g) as a white powdery product (yield 95%). The Boc group was deprotected with TFA, and 667 mg of thus-produced 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, 1.00 g) to afford the above-titled compound (Compound 11; 920 mg) as a colorless oily product (yield 58%).

Sources & evidence

ORD record: ord-607e8128d7fc4f179eba1ec8a1f65bbb
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668128

Reaction notes

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