Hydrogen Peroxide → HCID 86695217, compound

HRID 1504059Notes

Reaction equation

HRID 1504059 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:43])[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:27]3[C:26]4[C@@H:25]([CH2:28][CH:29]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30]#[N:31])[CH2:24][CH2:23][C:22]=4[S:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:44][Li].O.OO>CO>[C:1]([O:5][C:6]([N:8]([CH3:43])[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:27]3[C:26]4[C@@H:25]([CH2:28][C@H:29]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30](=[O:44])[NH2:31])[CH2:24][CH2:23][C:22]=4[S:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2].[C:1]([O:5][C:6]([N:8]([CH3:43])[CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:27]3[C:26]4[C@@H:25]([CH2:28][C@@H:29]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30](=[O:44])[NH2:31])[CH2:24][CH2:23][C:22]=4[S:21][C:20]=3[N:19]=[CH:18][N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 86695216HCID 86695216, compound

Product 2

HCID 86695217HCID 86695217, compoundHCID 86695218HCID 86695218, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 50-mL round-bottom flask containing a solution of benzyl N-[2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-cyano ethyl]carbamate (450 mg, 0.74 mmol, 1.00 equiv) in methanol (20 mL) was added LiOH.H2O (94 mg, 2.24 mmol, 3.00 equiv) and H2O2 (30%, 2 mL) at 0° C. The resulting solution was stirred for 2 h at 0° C. and quenched with saturated aqueous Na2SO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:3) to afford the corresponding benzyl N-[(1S)-2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-carbamoylethyl]carbamate (167.3, 230 mg) as a white solid and benzyl N-[(1R)-2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-carbamoylethyl]carbamate (167.4, 90 mg) as a white solid.

Workup

  1. customquenched with saturated aqueous Na2SO3
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65eb7a008f6f4eb18b94a51e2a077f44
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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