4-Amino-N-(3-amino-2-hydroxy-4-phenyl-butyl)-N-isobutyl-benzenesulfonamide → N-((2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)-4-aminobenzenesulfonamide

HRID 501992Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:16][CH:17]([OH:27])[CH:18]([NH2:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1>O>[NH2:26][C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@H:17]([OH:27])[CH2:16][N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 6 °C

Procedure

The obtained solution was then cooled to 40±3° C. followed by the addition of water. Adjustment of the pH of the solution to around 9.5 with aqueous solution of sodium hydroxide gave crystals 4-Amino-N-(3-amino-2-hydroxy-4-phenyl-butyl)-N-isobutyl-benzenesulfonamide. Additional water was added to this solution to adjust the concentration of 4-Amino-N-(3-amino-2-hydroxy-4-phenyl-butyl)-N-isobutyl-benzenesulfonamide to 5.5-5.8 wt %, and then this solution was cooled to 6±4° C. The resulting crystals were filtered off and washed with a mixed solution composed of water and ethanol and then washed with water. The resulting wet crystals were subjected to vacuum drying to give the product of (2R,3S)-N-(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-amino-benzenesulfonamide. Yields were 75˜85% based on (1-Benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl)-carbamic acid tert-butyl ester.

Workup

filtrationThe resulting crystals were filtered off
washwashed with a mixed solution
washwashed with water
customdrying

Sources & evidence

ORD record: ord-835b5c25f4f34e95a8e3e026e680b7ab
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772411B2

Reaction notes

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