1-Naphthalenemethanamine → HCID 22876889, compound

HRID 1378372Notes

Reaction equation

[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]([NH:20][C@H:21]([C:29](O)=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>>[C:13]([NH:20][C@H:21]([C:29]([NH:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14]

Participants

Reactant 2

HCID 83551-Naphthalenemethanamine

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 22876889HCID 22876889, compoundYield 91%

Procedure

In substantially the same manner as Working Example 2, 1-naphthalenemethylamine (4.32 g) was condensed with Boc-L-phenylalanine (6.63 g) to give N-(Boc-L-phenylalanyl)-1-naphthalenemethylamine (7.92 g) (yield 91%). The Boc group of the product was deprotected in substantially the same manner as Working Example 91 to give N-(L-phenylalanyl)-1-naphthalenemethylamine hydrochloride (4.24 g) (yield 64%). The compound thus obtained (0.75 g) was condensed, in substantially the same manner as Working Example 8, with monoethyl ester of (2S,3S)-N-benzylaziridine-2,3-dicarboxylic acid (0.50 g) obtained in Working Example 95 to give the above-titled compound (Compound 99; 0.79 g) as white crystals (yield 74%).

Sources & evidence

ORD record: ord-d0173690cad543bc8ec2cc9fa5269fd8
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668128

Reaction notes

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