Diisopropylethylamine → HCID 131730154, compound

HRID 1804581Notes

Reaction equation

HRID 1804581 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([C@H:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[O:37](C(OC(C)(C)C)=O)[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=O>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([C@H:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:9]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:37])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67972256HCID 67972256, compound

Product 1

HCID 131730154HCID 131730154, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound from Step C (1.20 g, 2.61 mmol) and N,N-diisopropylethylamine (0.910 ml, 5.21 mmol) in CH2Cl2 (15 ml) was added BOC2O (1.21 ml, 5.21 mmol) and the mixture was stirred at RT for overnight. The mixture was diluted with ethyl acetate (200 mL), washed with aqueous sodium hydrogen carbonate (saturated, 2×100 mL), with brine (100 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/isohexane 0%-10% to afford title compound as a colorless solid. Yield is 96%. LC-MS: m/z (E/S) 562.1 (MH)+.

Workup

  1. washwashed with aqueous sodium hydrogen carbonate (saturated, 2×100 mL), with brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel Biotage 40M
  6. washeluting with EtOAc/isohexane 0%-10%

Sources & evidence

ORD record
ord-c3d4187ebc4b4bb2b9252e5b7ab4d74a
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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