Triethylamine → HCID 86671485, compound

HRID 1530718Notes

Reaction equation

HRID 1530718 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]([NH:21][CH2:22][CH:23]=[CH2:24])[CH2:18][CH2:19][OH:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]([NH:21][CH2:22][CH:23]=[CH2:24])[CH2:18][CH2:19][O:20][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68312852HCID 68312852, compound

Product 1

HCID 86671485HCID 86671485, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-3-(1-allylamino-3-hydroxypropyl)piperidine-1-carboxylic acid benzyl ester (0.264 g, 0.794 mmol) in DCM (15 mL) cooled at 0° C. was added successively methanesulfonyl chloride (68 μL, 0.873 mmol) and Et3N (0.133 mL, 0.953 mmol). The mixture was stirred at RT for 1.5 h, and then diluted with DCM, washed with a saturated solution of NaHCO3, followed by water, then dried (Na2SO4) and concentrated in vacuo affording the title compound as a colourless gum (quantitative). LCMS (Method B): RT 2.14 min [M+H]+ 411.

Workup

  1. washwashed with a saturated solution of NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb75da6d091d431aa3fe48b138d8e264
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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