Triethylamine → HCID 68834205, compound

HRID 747757Notes

Reaction equation

HRID 747757 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. After stirring for 4 hours, the reaction mixture was treated by the isolation process with dichloromethane as the extractant in the same manner as that of step 1 in Example 1 to obtain an oily residue, which 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 isolation process with ethyl acetate as the extractant in the same manner as that of step 1 in Example 1, 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, which
  2. stirringwere stirred at 50° C. for 15 hours
  3. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-af06991f3e714d64bdd7f87c6adab472
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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