Isobutylamine → tert-Butyl (2S,3S)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-ylcarbamate

HRID 1368762Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3(S)-(t-butyloxycarbonyl)amino-1,2(S)-epoxy-4-phenylbutane (200 mg, 0.76 mmol) in 2 mL of dry isopropanol was added isobutylamine (0.38 mL, 3.8 mmol) and the mixture was stirred for 5 h at 50° C. The mixture was concentrated under reduced pressure and dried in vaccuo to give 230 mg of 2(S)-hydroxy-3(S)-(t-butyloxycarbonyl)amino-1-isobutylamino-4-phenylbutane

Workup

concentrationThe mixture was concentrated under reduced pressure
customdried in vaccuo

Sources & evidence

ORD record: ord-b1094d591248422798067bb25dd72d30
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573388B1

Reaction notes

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