2-Naphthylalanine → (1S,5S)-(1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid Methyl Ester

HRID 987962Notes

Reaction equation

HRID 987962 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:16]([CH2:22][OH:23])[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C=C2C(C=C(C[C@H](N)C(O)=O)C=C2)=CC=1.[CH3:40][O:41][C:42]([NH:44][CH:45]([CH2:49][C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=1)[C:46](O)=[O:47])=[O:43].C1C=C2C=CC=C(C[C@H](N)C(O)=O)C2=CC=1>>[CH3:40][O:41][C:42](=[O:43])[NH:44][C@H:45]([C:46](=[O:47])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:22][OH:23])[CH2:49][C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=1

Participants

5

Reactant 4

HCID 1859152-Naphthylalanine2×HCID 27248831-Naphthyl-L-alanineHCID 180090022-Methoxycarbonylamino-3-naphthalen-2-yl-propionic acidHCID 20595420(1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide

Product 1

HCID 513951(1S,5S)-(1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid Methyl Ester

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 L-2-naphthylalanine. The L-2-naphthylalanine was initially transformed into its 2-methoxycarbonylamino-3-naphthalen-2-yl-propionic acid derivative following the procedure used for L-1-naphthylalanine (example 28, step E). The final product was obtained in 41% yield (165 mg).

Sources & evidence

ORD record
ord-f38393835beb47b6821c390ed09840a3
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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