N-Methyl-N-naphthylmethylamine → HCID 22876892, compound

HRID 1378374Notes

Reaction equation

HRID 1378374 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[C:14]([NH:21][C@H:22]([C:38]([OH:40])=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>>[C:14]([NH:21][C@H:22]([C:38]([N:2]([CH3:1])[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:40])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:26][CH:25]=1)([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15]

Participants

3

Reactant 2

HCID 84474N-Methyl-N-naphthylmethylamineHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Product 1

HCID 22876892HCID 22876892, compound

Procedure

In substantially the same manner as Working Example 2, N-methyl-1-naphthalenemethylamine (877 μl) was condensed with Boc-(O-benzyl)-L-tyrosine (2.00 g) to give N-[Boc-(O-benzyl)-L-tyrosyl]-N-methyl-1-naphthalenemethylamine (2.60 g) as a white powdery product (yield 92%). The Boc group of the product was deprotected by using TFA, and 2.02 g of thus-obtained compound was condensed, in substantially the same manner as Working Example 2, with Compound 1 (1.40 g) to give N-[N-[(2S,3S)-N-Z-3-ethoxycarbonylaziridine-2-carbonyl]-(O-benzyl)-L-tyrosyl]-N-methyl-1-naphthalenemethylamine (1.73 g) as a white powdery product (yield 52%). This compound was subjected to catalytic reduciton to thereby deprotect the Z group and benzyl group in substantially the same manner as Working Example 3 to give the above-titled compound (compound 133; 580 mg) as white crystals (yield 53%).

Sources & evidence

ORD record
ord-0f3b48976cb543868d3e328cac30dfea
Source dataset
uspto-grants-1997_09
Patent number
US05668128

Reaction notes

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