N-[(1S)-2-[[(5S)-5-[(4-amino-3-chloro-phenyl)sulfonyl-isobutyl-amino]-6-hydroxy-hexyl]amino]-1-(1-naphthylmethyl)-2-oxo-ethyl]morpholine-4-carboxamide → (1S,5S)-(1-{5-[(4-Amino-3-chloro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic Acid Methyl Ester

HRID 987974Notes

Reaction equation

HRID 987974 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([C@@H](NC(N2CCOCC2)=O)CC2C3C(=CC=CC=3)C=CC=2)=O)(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:47].[CH3:48][O:49][C:50]([NH:52][C@@H:53]([CH:57]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:54](O)=[O:55])=[O:51]>>[CH3:48][O:49][C:50](=[O:51])[NH:52][C@H:53]([C:54](=[O:55])[NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]([N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([Cl:47])[CH:4]=1)(=[O:10])=[O:9])[CH2:43][CH:44]([CH3:45])[CH3:46])[CH2:41][OH:42])[CH:57]([C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

3

Reactant 2

HCID 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 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid

Product 1

HCID 513972(1S,5S)-(1-{5-[(4-Amino-3-chloro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic Acid Methyl Ester

Procedure

The title compound 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-methoxycarbonylamino-3,3-diphenyl-propionic acid (see example 34, step A). The final product was obtained in 43% yield (48 mg).

Sources & evidence

ORD record
ord-8b22f4b3117340f2aecf3895ecaf7793
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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