Dimethylamine → HCID 68284556, compound

HRID 1527518Notes

Reaction equation

HRID 1527518 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[F:23])[CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCO.CCOC(C)=O.[CH3:33][NH:34][CH3:35]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[F:23])[CH2:10][N:34]([CH3:35])[CH3:33])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 8857Ethyl AcetateHCID 86673867HCID 86673867, compound

Product 1

HCID 68284556HCID 68284556, compound

Procedure

A solution of methanesulfonic acid (S)-2-tert-butoxycarbonylamino-2-(3-chloro-2-fluoro-phenyl)-ethyl ester (690 mg, 1.88 mmol) in 33% dimethylamine in EtOH (5.6 M, 7.5 mL, 42 mmol) was heated at 80° C. for 2 h in a sealed tube. The reaction mixture was concentrated and the crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to EtOAc) to give a pale yellow oil. TLC, Rf (EtOAc): 0.60; MS (UPLC/MS): 317.3/319.3 [M+H]+; tR (HPLC conditions a): 3.19 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to EtOAc)
  3. customto give a pale yellow oil
  4. custom3.19 min.

Sources & evidence

ORD record
ord-1d8e01a2467a4038a7715b795960a1e3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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