Sodium sulfate decahydrate → (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate

HRID 245939Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]=[C:7]([C@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:11])[O:8][CH:9]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:16]([O:15][C:13](=[O:14])[NH:12][C@@H:10]([C:7]1[O:8][CH:9]=[C:5]([CH2:3][OH:2])[N:6]=1)[CH3:11])([CH3:17])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

In a round-bottomed flask, 2-((R)-1-tert-butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid methyl ester (151 mg, 0.56 mmol) was dissolved in THF (4 ml). The pale yellow solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.60 ml, 0.60 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution had ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred vigorously for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give 140 mg (93%) of [(R)-1-(4-hydroxymethyl-oxazol-2-yl)-ethyl]-carbamic acid tert-butyl ester as yellow oil which was used without further purification.

Workup

customthe ice bath was removed
additionsodium sulfate was added
stirringthe mixture was stirred vigorously for 30 min at room temperature
filtrationThe suspension was filtered over Celite
washrinsed with ethyl acetate/methanol
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-278991eb5df74b4c81db848bd5717321
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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