Triethylamine → HCID 86653279, compound

HRID 77331Notes

Reaction equation

HRID 77331 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([OH:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([O:27][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:8])=[O:9])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86653277(R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester

Product 1

HCID 86653279HCID 86653279, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)—N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester (0.90 g, 2.22 mmol) in dichloromethane (30 mL) at 0° C. is added triethylamine (0.463 mL, 3.3 mmol), methane sulfonyl chloride (0.269 g, 2.35 mmol), 4-dimethylaminopyridine (0.015 g, 0.12 mmol), and the reaction is allowed to warm to ambient temperature and stirred for 2 hours. The reaction is diluted with dichloromethane, washed with water and brine, and dried over magnesium sulfate. The solvents are removed in vacuo, and the residue is purified by column chromatography (35% hexanes-ethyl acetate) to afford the title compound as a colorless oil (0.95 g, 88% yield). LCMS (m/z): 484.17 (M+1), 482.16 (M−1).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents are removed in vacuo
  4. customthe residue is purified by column chromatography (35% hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-6ded1bf21f4542e0ba5c75ed0bca083d
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Reaction notes

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