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-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-biphenyl-4-yl-ethyl)-carbamic Acid tert-Butyl Ester

HRID 987977Notes

Reaction equation

HRID 987977 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]=1Cl.[C:48]1([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:53]=[CH:52][C:51]([CH2:54][C@H:55]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C:56]([OH:58])=O)=[CH:50][CH:49]=1>>[C:63]([O:62][C:60](=[O:61])[NH:59][C@H:55]([C:56](=[O:58])[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])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:43][CH:44]([CH3:45])[CH3:46])[CH2:41][OH:42])[CH2:54][C:51]1[CH:50]=[CH:49][C:48]([C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)=[CH:53][CH:52]=1)([CH3:66])([CH3:64])[CH3:65]

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 2761796N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH)

Product 1

HCID 513981(1S,5S)-(1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-biphenyl-4-yl-ethyl)-carbamic Acid tert-Butyl Ester

Procedure

The title compound was prepared from the amine, (1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide (XII) (example 28, step D), and the acid, (2S)-3-biphenyl-4-yl-2-tert-butoxycarbonylamino-propionic acid, as described in general procedure E. The final product was obtained in 67% yield.

Sources & evidence

ORD record
ord-df5e54123e0a42f79467362023148766
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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