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

HRID 987966Notes

Reaction equation

HRID 987966 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].[N:25]1([C:31]([NH:33][C@@H:34]([CH2:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=2)[C:35]([OH:37])=[O:36])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C1C=C2C(C=C(C[C@H](N)C(O)=O)C=C2)=CC=1.[N:65]1([C:71]([NH:73][C@@H:74]([CH2:78][C:79]2[C:88]3[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=3)[CH:82]=[CH:81][CH:80]=2)[C:75]([OH:77])=O)=[O:72])[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1>>[N:25]1([C:31]([NH:33][C@@H:34]([CH2:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=2)[C:35]([OH:37])=[O:36])=[O:32])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1.[OH:8][CH2:7][C@@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:75]([C@@H:74]([NH:73][C:71]([N:65]1[CH2:66][CH2:67][O:68][CH2:69][CH2:70]1)=[O:72])[CH2:78][C:79]1[CH:80]=[CH:81][C:82]2[C:87](=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:88]=1)=[O:77]

Participants

6

Reactant 4

HCID 1859152-NaphthylalanineHCID 12986165(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acidHCID 67531312(1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-4-methoxy-benzenesulfonamideHCID 67532430(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid

Product 2

HCID 513957N-[(1S)-2-[[(5S)-6-hydroxy-5-[isobutyl-(4-methoxyphenyl)sulfonyl-amino]hexyl]amino]-1-(2-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamideHCID 67532430(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid

Procedure

This derivative was prepared from (1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-4-methoxy-benzenesulfonamide (XII) (this example, step B) as described in general procedure B using (2S)-2-[(morpholine4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid. The (2S)-2-[(morpholine-4-carbonyl)-amino]-3-naphthalen-2-yl-propionic acid 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 (example 32, step A). The final product was obtained in 46% yield (47 mg).

Sources & evidence

ORD record
ord-0ec28620ed0e4090b06bfa68c59b064d
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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