Benzylamine → (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide

HRID 1378373Notes

Reaction equation

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

Participants

Reactant 2

HCID 7504Benzylamine

HCID 7020908Boc-3-(2-naphthyl)-L-alanine

Product 1

HCID 10692607(2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamideYield 94%

Procedure

In substantially the same manner as Working Example 2, benzylamine (0.93 g) was condensed with Boc-3-(2-naphthyl)-L-alanine (2.50 g) to give N-(Boc-3-(2-naphthyl)-L-alanyl)benzylamine (3.0 g) as white crystals (yield 94%). The Boc group of the product was deprotected by using 4N hydrochloric acid/ethyl acetate solution, and 1.82 g of thus-obtained compound was condensed, in substantially the same manner as Working Example 2, with Compound 1 (1.47 g) to give the above-titled compound (Compound 109; 0.85 g) as white crystals (yield 29%).

Sources & evidence

ORD record: ord-d8487c27c2634f2abaea8a60fa8cb91b
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668128

Reaction notes

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