Triethylamine → HCID 59710219, compound

HRID 1864505Notes

Reaction equation

HRID 1864505 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]([Si:10]([CH3:27])([CH3:26])[O:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:13]1[CH2:24][OH:25])([CH3:9])[CH3:8].C(N(CC)CC)C>>[CH3:9][C:7]([Si:10]([CH3:27])([CH3:26])[O:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C@@H:13]1[CH2:24][O:25][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[CH3:8]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

Product 1

HCID 59710219HCID 59710219, compound

Procedure

Methanesulfonyl chloride (3.85 mL, 39.29 mmol) was added to an ice cold methylene chloride solution of 1,1-dimethylethyl(2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy-}2-(hydroxymethyl)-1-pyrrolidinecarboxylate (6.05 g, 26.19 mmol) and triethylamine (7.28 mL, 52.38 mmol). The reaction was warmed to room temperature, stirred for 16 hours then concentrated under reduced pressure. The crude material was dissolved in ethyl acetate and washed with saturated NaHCO3, dried over MgSO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to give the title compound as a yellow oil. (4.69 g, 11.4 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.1 (s, 6H), 0.8 (s, 9H), 1.4 (m, 9H), 1.7 (m, 1H), 2.0 (m, 1H), 3.2 (s, 3H), 3.3 (m, 2H), 3.7 (m, 1H), 4.0 (m, 1H), 4.2 (m, 1H), 4.3 (m, 1H). ES+=410.16.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef2b21b88a1f45529a1a10d8ac1510f3
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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