Triethylamine → HCID 86632800, compound

HRID 253598

Reaction equation

HRID 253598 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][N:8]([CH2:18][C@@H:19]([OH:29])[C@@H:20]([NH2:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:9]([O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH3:32][O:33][C:34]1[C:35](=O)[C:36](=[O:40])[C:37]=1[O:38]C.CCN(CC)CC>CCO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:18][C@@H:19]([OH:29])[C@@H:20]([NH:28][C:35]2[C:36](=[O:40])[C:37](=[O:38])[C:34]=2[O:33][CH3:32])[CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:9]([O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])=[CH:30][CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 66861734HCID 66861734, compound

Product 1

HCID 86632800HCID 86632800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2R,3S)-1-(N-(4-cyanobenzyl)-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-2-hydroxy-3-amino-4-cyclohexylbutane (764 mg, 1.68 mmol) in EtOH (20 mL) was treated with 3,4-dimethoxycyclobut-3-ene-1,2-dione (300 mg, 2.10 mmol, 1.25 equiv) and Et3N (212 mg, 1.25 equiv). The resulting solution was allowed to stir at rt for 17 h. The excess 3,4-dimethoxycyclobut-3-ene-1,2-dione was removed by flash chromatography on silica gel, eluting with 0-65% EtOAc in hexanes. Analysis of the compound by LC-MS showed that it was of sufficient purity to employ in the subsequent steps.

Workup

  1. customThe excess 3,4-dimethoxycyclobut-3-ene-1,2-dione was removed by flash chromatography on silica gel
  2. washeluting with 0-65% EtOAc in hexanes

Sources & evidence

ORD record
ord-f3a06eccc2fa4bc788578fc76fb70eb3
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Linked notes

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