2-Naphthylalanine → N-[(1S)-2-[[(5S)-5-[(4-amino-3-chloro-phenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(2-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamide

HRID 987975Notes

Reaction equation

HRID 987975 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:43][CH:44]([CH3:46])[CH3:45])[C@H:12]([CH2:41][OH:42])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@@H:20]([NH:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])[CH2:21]C2C3C(=CC=CC=3)C=CC=2)=[O:19])(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:47].N1(C(N[C@@H](C[C:62]2[CH:71]=[CH:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH:63]=2)C(O)=O)=O)CCOCC1.C1C=C2C(C=C(C[C@H](N)C(O)=O)C=C2)=CC=1.N1(C(N[C@@H](CC2C3C(=CC=CC=3)C=CC=2)C(O)=O)=O)CCOCC1.C1C=C2C=CC=C(C[C@H](N)C(O)=O)C2=CC=1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:43][CH:44]([CH3:46])[CH3:45])[C@H:12]([CH2:41][OH:42])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@@H:20]([NH:32][C:33]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)=[O:34])[CH2:21][C:62]2[CH:71]=[CH:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH:63]=2)=[O:19])(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:47]

Participants

6

Reactant 5

HCID 1859152-NaphthylalanineHCID 513966N-[(1S)-2-[[(5S)-5-[(4-amino-3-chloro-phenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(1-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamideHCID 27248831-Naphthyl-L-alanineHCID 12986165(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acidHCID 67532430(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid

Product 1

HCID 513973N-[(1S)-2-[[(5S)-5-[(4-amino-3-chloro-phenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(2-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamideYield 25%

Procedure

This derivative was prepared from (1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-3-chloro-N-isobutyl-benzenesulfonamide (XII) (example 44, step B) as described in general procedure B using (2S)-2-[(morpholine-4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid. The latter derivative was prepared from L-2-naphthylalanine as described for the preparation of (2S)-2-[(morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid from L-1-naphthylalanine. The final product was obtained in 25% yield (51 mg).

Sources & evidence

ORD record
ord-75f1524aec05426aaab892a003fe58d0
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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