Triethylamine → HCID 68834205, compound

HRID 747723Notes

Reaction equation

HRID 747723 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:34]O)[CH2:10][C:11]1[CH:33]=[CH:32][C:14]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS([Cl:47])(=O)=O.[Cl-].[Li+]>ClCCl.CN(C)C=O.C(OCC)(=O)C>[Cl:47][CH2:34][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][C:11]1[CH:33]=[CH:32][C:14]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 68830405benzyl 4-[4-[(2S)-2-(t-butoxycarbonylamino)-3-hydroxypropyl]phenoxy]piperidine-1-carboxylate

Product 1

HCID 68834205HCID 68834205, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5.5 g (11.3 mmol) of benzyl 4-[4-[(2S)-2-(t-butoxycarbonylamino)-3-hydroxypropyl]phenoxy]piperidine-1-carboxylate was dissolved in 60 ml of dichloromethane. 3.2 ml (22.6 mmol) of triethylamine and 1.95 g (17.0 mmol) of methanesulfonyl chloride were added to the solution at 0° C. After stirring for 4 hours, the reaction mixture was treated with dichloromethane as the extractant in an ordinary manner to obtain an oily residue. The residue thus obtained was dissolved in 120 ml of dimethylformamide. 2.57 g (60.6 mmol) of lithium chloride was added to the solution, and they were stirred at 50° C. for 15 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customto obtain an oily residue
  2. customThe residue thus obtained
  3. stirringwere stirred at 50° C. for 15 hours
  4. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-b257fe7ffac1492382fb2fa6fa8a760a
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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