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4-Methylmorpholine → HCID 86619630, compound

HRID 2265891
Notes
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Reaction equation

HRID 2265891 reaction equation
ClC(OCC)=O.[F:7][C:8]1[CH:45]=[CH:44][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([N:22]3[CH2:31][CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]=4[O:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[CH:23]3[C:41]([OH:43])=O)(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.CN1CCOCC1.C[Si](C)(C)[O:55][NH2:56]>CN(C=O)C>[OH:55][NH:56][C:41]([CH:23]1[C:24]2[C:29](=[C:28]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[CH:27]=[CH:26][CH:25]=2)[CH2:30][CH2:31][N:22]1[S:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][C:11]2[CH:44]=[CH:45][C:8]([F:7])=[CH:9][CH:10]=2)=[CH:18][CH:17]=1)(=[O:20])=[O:21])=[O:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 66878721HCID 66878721, compound

Product 1

HCID 86619630HCID 86619630, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
-20 °C

Procedure

8.16 μl (85.6 μmol) of ethyl chloroformate are added to a solution of 38 mg (68.5 μmol) of 2-[4-(4-fluorophenoxy)benzenesulfonyl]-5-(2-piperidin-1-ylethoxy)-1,2,3,4-tetra-hydroisoquinoline-1-carboxylic acid and 16.6 μl (151 μmol) of N-methylmorpholine in 2 ml of DMF at −20° C., and the mixture is stirred at −20° C. for 30 minutes. Then 37.2 μl (274 μmol) of O-trimethylsilylhydroxylamine are added, and the solution is warmed slowly to room temperature. After standing overnight, it is concentrated in vacuo and the residue is purified by chromatography on silica gel, allowing the title compound to be isolated as a colorless solid. Yield 46%.

Workup

  1. temperaturethe solution is warmed slowly to room temperature
  2. waitAfter standing overnight
  3. concentrationit is concentrated in vacuo
  4. customthe residue is purified by chromatography on silica gel
  5. customto be isolated as a colorless solid

Sources & evidence

ORD record
ord-ff713437bd0849cc804883d392787b76
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858619B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes