Methanol → HCID 86695106, compound

HRID 1503929Notes

Reaction equation

I[CH:2]([C:32]1[O:33][CH:34]=[CH:35][N:36]=1)[CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([O:16][CH:17]4[CH2:22][CH2:21][CH:20]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]4)[C:6]=3[C:5]1=2.CO.[BH4-].[Na+]>O1CCCC1>[CH3:31][N:23]([CH:20]1[CH2:21][CH2:22][CH:17]([O:16][C:7]2[C:6]3[C:5]4[C@@H:4]([CH2:3][CH2:2][C:32]5[O:33][CH:34]=[CH:35][N:36]=5)[CH2:15][CH2:14][C:13]=4[S:12][C:11]=3[N:10]=[CH:9][N:8]=2)[CH2:18][CH2:19]1)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A 25-mL round-bottom flask containing a solution of tert-butyl N-(4-[[(3R)-3-[2-iodo-2-(1,3-oxazol-2-yl)ethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (150 mg, 0.24 mmol, 1.00 equiv) in a mixed methanol (5 mL) and tetrahydrofuran (5 mL) was added NaBH4 (40 mg, 1.08 mmol, 4.50 equiv) at 0° C. The resulting solution was stirred for 4 h at 0° C. and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10 to 1:22) to afford the desired tert-butyl N-methyl-N-(4-[[(3S)-3-[2-(1,3-oxazol-2-yl)ethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (110 mg, 92%) as a yellow solid. MS (ES, m/z): 499 (M+H)+.

Workup

concentrationconcentrated under reduced pressure
additionThe residue was diluted with EtOAc
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-fd488ba2e90c4930a0215219f04720da
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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