Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68291990, compound

HRID 1507974Notes

Reaction equation

CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[C:16]([O:20][C:21]([NH:23][C@H:24]([CH3:38])[C@@H:25]([CH2:36][CH3:37])[C:26]([NH:28][C@@H:29]([CH2:34][OH:35])[C:30]([O:32][CH3:33])=[O:31])=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([NH:23][C@@H:24]([C@H:25]([C:26]1[O:35][CH2:34][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:28]=1)[CH2:36][CH3:37])[CH3:38])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

Burgess reagent (1.35 g, 5.66 mmol) was added in one portion to a solution of (S)-methyl 2-((2R,3R)-3-((tert-butoxycarbonyl)amino)-2-ethylbutanamido)-3-hydroxypropanoate (1.71 g, 5.14 mmol) in anhydrous THF (79 ml) under a nitrogen atmosphere. The reaction was then allowed to stir at 60° C. for about 4 hr. TLC indicated complete consumption of starting material and a less polar spot (1:1 hexane:ethyl acetate; KMnO4 staining). After cooling to 0° C., saturated aqueous sodium bicarbonate solution (30 mL) was added and the mixture extracted with ethyl acetate (3×25 mL). The combined organics were then dried (MgSO4) and evaporated in vacuo to give (S)-methyl 2-((2R,3R)-2-((tert-butoxycarbonyl)amino)pentan-3-yl)-4,5-dihydrooxazole-4-carboxylate (1.62 g, 5.14 mmol, 100% yield) as an oil which was used immediately in the next step.

Workup

customconsumption of starting material
temperatureAfter cooling to 0° C.
additionsaturated aqueous sodium bicarbonate solution (30 mL) was added
extractionthe mixture extracted with ethyl acetate (3×25 mL)
dry with materialThe combined organics were then dried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-c48dba7d8abe44f2b7a49bc624fc399e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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