Diisopropylethylamine → HCID 131730154, compound

HRID 1911836Notes

Reaction equation

HRID 1911836 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)
  2. dry with materialwith) brine (100 mL), dried (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-5380d10f47d04756bfe3525c73c89a4c
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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