Furfurylamine → HCID 22876890, compound

HRID 1378368Notes

Reaction equation

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

Participants

Reactant 2

HCID 3438Furfurylamine

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

Product 1

HCID 22876890HCID 22876890, compoundYield 89%

Procedure

In substantially the same manner as Working Example 2, furfurylamine (2.91 g) was condensed with Boc-L-phenylalanine (8.75 g) to give N-(Boc-L-phenylalanyl)furfurylamine (9.14 g) (yield 89%). The Boc group of the product was deprotected by using TFA, and 0.43 g of thus-deprotected compound was condensed, in substantially the same manner as Working Example 42, with monoethyl ester of (2S,3S)-N-methylaziridine-2,3-dicarboxylic acid (0.28 g) to give the above-titled compound (Compound 89; 0.23 g) as white crystals (yield 36%).

Sources & evidence

ORD record: ord-8751633995d24085b4b66f3842875dcb
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668128

Reaction notes

Loading…