4-Methylmorpholine → HCID 86619630, compound

HRID 2265891Notes

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]

Participants

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

temperaturethe solution is warmed slowly to room temperature
waitAfter standing overnight
concentrationit is concentrated in vacuo
customthe residue is purified by chromatography on silica gel
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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