Diisopropyl Ether → N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

HRID 1281197Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:10]([OH:13])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(C)C)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>C(OCC)(=O)C.CCCCCCC>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C@@H:10]([OH:13])[CH2:11][O:12][S:29]([CH3:28])(=[O:31])=[O:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of the crude N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-butanol obtained in Reference Example 3 and dissolved in ethyl acetate 250 kg were added isopropylether 230 kg, methane sulfonylchloride 34.7 kg at 20-30° C., and triethylamine 30.6 kg and stirring at 30-40° C. for 1 hr. N-heptane was added to the reaction solution and the obtained solution was cooled down to 5° C. or lower to deposit crystals, which were filtered by centrifugation to obtain a wet crystal of crude N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane 153.6 kg (Net.60.6 kg).

Workup

filtrationwere filtered by centrifugation

Sources & evidence

ORD record: ord-455bfafc05564994908709d2f85b738c
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06452026B1

Reaction notes

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