(S)-3-tert-Butoxycarbonylamino-2-hydroxy-pentanoic acid → (S)-2-Amino-1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-butan-1-ol

HRID 1765678Notes

Reaction equation

C(OC([NH:8][CH:9]([CH2:15][CH3:16])[C@H:10]([OH:14])[C:11]([OH:13])=O)=O)(C)(C)C.O[NH:18][C:19]([CH:21]1[CH2:23][CH2:22]1)=[NH:20]>ClCCl>[NH2:8][CH:9]([CH2:15][CH3:16])[C@@H:10]([C:11]1[O:13][N:20]=[C:19]([CH:21]2[CH2:23][CH2:22]2)[N:18]=1)[OH:14]

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of (S)-3-tert-Butoxycarbonylamino-2-hydroxy-pentanoic acid (2.00 g, 8.57 mmol) and N-hydroxy-cyclopropanecarboxamidine (1.03 g, 10.29 mmol) in dichloromethane (20 mL) was stirred at 0° C. and 1.25 equivalents of N-cyclohexylcarbodiimide-N′-methyl polystyrene (1.70 mmol/g, 6.30 g, 10.72 mmol) was added in portions. The reaction mixture stirred under nitrogen for three hours while warming to 15° C. The reaction mixture was filtered, the resin washed with dichloromethane and the filtrate evaporated under vacuum to dryness. [LC/MS m/z=338 (M+H+Na)].

Workup

filtrationThe reaction mixture was filtered
washthe resin washed with dichloromethane
customthe filtrate evaporated under vacuum to dryness

Sources & evidence

ORD record: ord-593bd0858a82408bacd6f9d901b01187
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226921B2

Reaction notes

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