Pyridine → HCID 67508320, compound

HRID 1770693Notes

Reaction equation

HRID 1770693 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][S:10]([CH2:13][CH2:14][C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:17])[CH3:16])(=[O:12])=[O:11].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>ClCCl>[C:35]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][S:10]([CH2:13][CH2:14][C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:16])[CH3:17])(=[O:11])=[O:12])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 7918Acetic Anhydride2×HCID 67509059HCID 67509059, compound

Product 1

HCID 67508320HCID 67508320, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-ylcarbamate (451 mg, 1.08 mmol) in dichloromethane (5 ml) was cooled to 0° C. Pyridine (200 μl, 2.48 mmol), then acetic anhydride (150 μl, 1.59 mmol) were added. The solution was stirred for 3 hours, and another portion of pyridine (200 μl, 2.48 mmol) then acetic anhydride (150 μl, 1.59 mmol) were added. The solution was stirred for an additional 20 hours, concentrated in vacuo, and the residue purified by flash chromatography (20% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (440.2 mg, 0.959 mmol, 89%). 1H NMR (CDCl3, 400 MHz) δ 1.31 (s, 6H), 2.04 (s, 3H), 2.15-2.20 (m, 2H), 3.09-3.16 (m, 4H), 3.54-3.61 (m, 6H), 3.85 (t, J=5.6 Hz, 2H), 4.16 (m, 2H), 5.02 (s, 3H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 460 [M+H]+, 482 [M+Na]+.

Workup

  1. stirringThe solution was stirred for an additional 20 hours
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by flash chromatography (20% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-14d4f9c9f6dc4b788ead2f1ba6bd768a
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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