Sulfuric Acid → HCID 67517747, compound

HRID 1770716Notes

Reaction equation

HRID 1770716 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].S(=O)(=O)(O)O>C(O)(C)(C)C>[C:15]([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])([CH3:17])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67509059HCID 67509059, compound

Product 1

HCID 67517747HCID 67517747, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of benzyl 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-ylcarbamate (132.3 mg, 0.317 mmol) in tert-butanol (500 ul) was added conc. sulfuric acid (100 ul). The solution was stirred at RT for 6 d, concentrated in vacuo, and the residue purified by flash chromatography (30%→80% EtOAc in hexanes) to afford the title compound as a clear oil (79.5 mg, 0.168 mmol, 53%). 1H NMR (CDCl3, 400 MHz) δ 1.18 (s, 9H), 1.27 (s, 6H), 2.17-2.20 (m, 2H), 3.12-3.18 (m, 4H), 3.46-3.49 (m, 2H), 3.53-3.56 (m, 2H), 3.60 (s, 4H), 3.89 (t, J=6.8 Hz, 2H), 5.01-5.04 (m, 3H), 7.3-7.4 (m, 5H). LRMS (ESI/APCI): 496 [M+Na]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (30%→80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7e1c667aa7934fce8206664e032fab12
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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