L-Phenylalanine → N-[(1S)-1-[[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]carbamoyl]-2,2-diphenyl-ethyl]morpholine-4-carboxamide

HRID 987967Notes

Reaction equation

HRID 987967 reaction equation
[OH:1][CH2:2][C@@H:3]([N:32]([CH2:44][CH:45]([CH3:47])[CH3:46])[S:33]([C:36]1[CH:41]=[CH:40][C:39](OC)=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8]C([C@@H](NC(N1CCOCC1)=O)CC1C=CC2C(=CC=CC=2)C=1)=O.[N:48]1([C:54]([NH:56][C@@H:57]([CH:61]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:58]([OH:60])=[O:59])=[O:55])[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.C1C=CC(C[C@H]([NH2:85])C(O)=O)=CC=1.N1(C(N[C@@H](CC2C3C(=CC=CC=3)C=CC=2)C(O)=O)=O)CCOCC1>>[N:48]1([C:54]([NH:56][C@@H:57]([CH:61]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[C:58]([OH:60])=[O:59])=[O:55])[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.[NH2:85][C:39]1[CH:40]=[CH:41][C:36]([S:33]([N:32]([CH2:44][CH:45]([CH3:47])[CH3:46])[C@H:3]([CH2:2][OH:1])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:58]([C@@H:57]([NH:56][C:54]([N:48]2[CH2:49][CH2:50][O:51][CH2:52][CH2:53]2)=[O:55])[CH:61]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:59])(=[O:35])=[O:34])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 6140L-PhenylalanineHCID 513957N-[(1S)-2-[[(5S)-6-hydroxy-5-[isobutyl-(4-methoxyphenyl)sulfonyl-amino]hexyl]amino]-1-(2-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamideHCID 12986165(2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acidHCID 12986168(2s)-2-[(Morpholine-4-carbonyl)-amino]-3,3-diphenyl-propionic acid

Product 2

HCID 513962N-[(1S)-1-[[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]carbamoyl]-2,2-diphenyl-ethyl]morpholine-4-carboxamideHCID 12986168(2s)-2-[(Morpholine-4-carbonyl)-amino]-3,3-diphenyl-propionic acid

Procedure

The title compound 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 (2S)-2-[(morpholine-4-carbonyl)-amino]-3,3-diphenyl-propionic acid. The (2S)-2-[(morpholine-4-carbonyl)-amino]-3,3-diphenyl-propionic acid derivative was prepared from L-diphenylalanine 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 28% yield (14 mg).

Sources & evidence

ORD record
ord-f11c1298ee324b6f986cf29f9955be80
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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