Sodium Hydroxide → HCID 11213585, compound

HRID 898158Notes

Reaction equation

HRID 898158 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:9][CH2:10][N:11]1[CH2:30][CH2:29][C:14]2([NH:18][C:17](=[O:19])[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[C:15]2=[O:28])[CH2:13][CH2:12]1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.[OH-].[Na+]>>[NH2:7][C@H:8]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][C:14]2([NH:18][C:17](=[O:19])[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[C:15]2=[O:28])[CH2:29][CH2:30]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 11410532HCID 11410532, compoundHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 11213585HCID 11213585, compoundYield 102.9%

Procedure

To 116 mg (0.2 mmol) of {3-[3-(4-bromobenzyl)-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-yl]-1-(S)-phenylpropyl}-carbamic acid tert-butyl ester were added 2 mL of a solution DCM/TFA 20%. The reaction mixture was agitated one hour at room temperature before neutralizing with 1.8 mL of a 10% aqueous solution of sodium hydroxide. Then the solution was extracted with DCM, dried over sodium sulfate, filtered and evaporated in vacuo yielding Compound 5 as a white solid (97 mg, 100%).

Workup

  1. extractionThen the solution was extracted with DCM
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-dc57a7133383494fa5e0a61656ddfa74
Source dataset
uspto-grants-2008_04
Patent number
US07351713B2

Reaction notes

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