Sodium hydride → HCID 86695225, compound

HRID 1504065Notes

Reaction equation

[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.Cl[C:19]1[C:20]2[C:21]3[C@H:22]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:23][CH2:24][CH2:25][C:26]=3[S:27][C:28]=2[N:29]=[CH:30][N:31]=1>C1COCC1>[C:13]([O:12][C:11]([NH:10][CH:7]1[CH2:8][CH2:9][CH:4]([O:3][C:19]2[C:20]3[C:21]4[C@H:22]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:23][CH2:24][CH2:25][C:26]=4[S:27][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:5][CH2:6]1)=[O:17])([CH3:14])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

NaH (60% dispersion in mineral oil, 438 mg, 10.95 mmol, 4.00 equiv) was treated with tert-butyl N-(4-hydroxycyclohexyl)carbamate (710 mg, 3.30 mmol, 1.20 equiv) in freshly distilled THF at 50° C. for 30 min under nitrogen. Then a solution of ethyl 2-[(13S)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate (850 mg, 2.73 mmol, 1.00 equiv) in THF (10 mL) was added via syringe and stirred for 2 h at 60° C. After cooling, the reaction was quenched with brine, extracted with ethyl acetate (80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to give 800 mg (60%) of ethyl 2-[(13S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate as a colorless oil.

Workup

temperatureAfter cooling
customthe reaction was quenched with brine
extractionextracted with ethyl acetate (80 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e987f0e090f0409fb1137a9bd65b0de4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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