Methanol → HCID 86626189, compound

HRID 2355348Notes

Reaction equation

HRID 2355348 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].[CH3:11][Si:12]([CH3:29])([CH3:28])[CH2:13][CH2:14][O:15][CH2:16][NH:17][CH2:18][C@@H:19]([NH2:27])[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.C[OH:38]>>[CH:21]1([CH2:20][C@H:19]([NH:27][C:3]2[C:4](=[O:10])[C:5](=[O:9])[C:6]=2[O:7][CH3:8])[CH2:18][NH:17][C:16](=[O:38])[O:15][CH2:14][CH2:13][Si:12]([CH3:28])([CH3:11])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 68711280HCID 68711280, compound

Product 1

HCID 86626189HCID 86626189, compoundYield 80%

Procedure

Solid 3,4-dimethoxycyclobut-3-ene-1,2-dione (87.5 mg, 0.61 mmol) was added to a solution of (S)—N1-((2-(trimethylsilyl)ethoxy)methyl)-3-cyclohexylpropane-1,2-diamine (173.1 mg, 0.57) and triethylamine (0.2 mL, 1.4 mmol) in MeOH (10 mL). After stirring at rt for 2 h, the solvent was removed and the residue was purified using 4 g SiO2 with an eluent of hexanes to EtOAc. Removal of solvent from appropriate fractions yielded (S)-2-(trimethylsilyl)ethyl 3-cyclohexyl-2-(2-methoxy-3,4-dioxocyclobut-1-enylamino)propylcarbamate (186.2 mg, 80%) as a clear film. MS ESI+ve m/z 433 (M+Na).

Workup

  1. customthe solvent was removed
  2. customthe residue was purified
  3. customRemoval of solvent from appropriate fractions

Sources & evidence

ORD record
ord-f2e6ec66459745f5b4a959e5bd35a913
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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