Water → HCID 67211640, compound

HRID 2066002Notes

Reaction equation

HRID 2066002 reaction equation
[C:1]([O:5][C:6](=[O:49])[N:7]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])([CH3:4])([CH3:3])[CH3:2].[O:50](C(OC(C)(C)C)=O)[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=O.O>C1COCC1>[C:54]([O:53][C:51](=[O:50])[N:16]([CH2:15][CH2:14][CH2:13][N:12]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:49])[CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29])([CH3:57])([CH3:56])[CH3:55]

Participants

5

Reactant 3

HCID 962WaterHCID 90495Di-tert-butyl dicarbonateHCID 67211529HCID 67211529, compound

Product 1

HCID 67211640HCID 67211640, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in Stage 1 above (2.31 g, 3.3 mmol, 1 eq) is dissolved in 50 mL of THF with stirring. A solution of BOC2O (0.8 g, 3.7 mmol, 1.1 eq) in 10 mL of THF is then added dropwise at room temperature. Stirring is continued for 4 hrs and then the medium is poured into water and extracted with AcOEt (3×100 mL), dried (Na2SO4), filtered, and evaporated. The residue is flash chromatographed with a gradient from pure heptane to pure AcOEt. 1.49 g (Yield 56%) is obtained after evaporation.

Workup

  1. stirringStirring
  2. extractionextracted with AcOEt (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed with a gradient from pure heptane to pure AcOEt
  7. custom1.49 g (Yield 56%) is obtained
  8. customafter evaporation

Sources & evidence

ORD record
ord-6fea57c3db944927a7985ab3a2ae9b2e
Source dataset
uspto-grants-2012_10
Patent number
US08288567B2

Reaction notes

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