Triethylamine → HCID 59710219, compound
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
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, 6 H) 0.8 (s, 9 H) 1.4 (m, 9 H) 1.7 (m, 1 H) 2.0 (m, 1 H) 3.2 (s, 3 H) 3.3 (m, 2 H) 3.7 (m, 1 H) 4.0 (m, 1 H) 4.2 (m, 1 H) 4.3 (m, 0.1 H). ES+=410.16.
Workup
- concentrationthen concentrated under reduced pressure
- dissolutionThe crude material was dissolved in ethyl acetate
- washwashed with saturated NaHCO3
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ea678983a75446879c224b0c2be019fb
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368453B2
Reaction notes
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