2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid → N-[(1S)-2-[[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(1-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamide

HRID 987963Notes

Reaction equation

HRID 987963 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:16]([CH2:22][OH:23])[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:24]1([C:30]([NH:32][CH:33]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)[C:34](O)=[O:35])=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C@H:16]([CH2:22][OH:23])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:34]([C@@H:33]([NH:32][C:30]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[O:31])[CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)=[O:35])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 180090242-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acidHCID 20595420(1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide

Product 1

HCID 513954N-[(1S)-2-[[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(1-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamideYield 32%

Procedure

This material was prepared from (1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide (XII) (example 28, step D) as described in general procedure B using 2-[(morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid (step A). The final product was obtained in 32% yield (33 mg).

Sources & evidence

ORD record
ord-58ab94a11e2746818ba90819243c52fb
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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