HCID 86695200, compound → HCID 86695201, compound

HRID 1504044Notes

Reaction equation

HRID 1504044 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[N:16]=[CH:15][N:14]=[C:13]([O:22][CH:23]4[CH2:28][CH2:27][C:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:25][CH2:24]4)[C:12]=3[C:11]1=2)(C(C)(C)C)(C)C>O1CCCC1>[OH:8][CH2:9][C@H:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[N:16]=[CH:15][N:14]=[C:13]([O:22][CH:23]4[CH2:24][CH2:25][C:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:27][CH2:28]4)[C:12]=3[C:11]1=2

Participants

3

Reactant 1

HCID 86695200HCID 86695200, compound

Product 1

HCID 86695201HCID 86695201, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(4-[[(3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate (1.20 g, 2.19 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was added TBAF-3H2O (1.09 g, 3.45 mmol, 1.58 equiv) at 0° C. and the resulting solution was stirred for 3 h at room temperature. The reaction was quenched with water and extracted with 3×100 mL of ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. Purification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:20 to 1:5) afforded tert-butyl N-(4-[[(3S)-3-(hydroxymethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate (900 mg, 95%) as a colorless oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with 3×100 mL of ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customPurification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:20 to 1:5)

Sources & evidence

ORD record
ord-c6188db9caa4434cb31e0876c91efd50
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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