Diethyl Ether → HCID 57059046, compound

HRID 1654644Notes

Reaction equation

HRID 1654644 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:10]([O:13]C(=O)C)[CH:11]=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)[CH:25]([CH3:27])[CH3:26].[CH3:30]COCC>CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:10]([OH:13])[C@@H:11]([OH:12])[CH:25]([CH3:26])[CH2:27][CH3:30])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 14856784(2R,3S)-N-(tert-Butyloxy)carbonyl-3-amino-2-acetoxy-4-phenylbutanalHCID 178418368HCID 178418368, compound

Product 1

HCID 57059046HCID 57059046, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The title compound of Step 1 was dissolved to -70° C. this solution was added 13 mL (26 mmol) of a 2.0M solution of isobutylmagnesium chloride in ether and the stirred mixture was allowed to warm to room temperature and stir for 2 hrs. After decomposition with MeOH/H2O the mixture was diluted with ether, washed with saturated NH4Cl solution twice and dried with magnesium sulfate and the solvents evaporated under vacuum. The residue was allowed to stand overnight in 80% NeOH-H2O containing excess ammonium hydroxide. The MeOH was stripped off and the mixture was exracted with ether. These extracts were combined, washed with water, dilute KHSO4, then dried and evaporated to give 2.36 g of a yellow glass which crystallized from 50 mL of pentane on standing overnight. The yellow-white powder obtained was recrystallized from ether-hexane and furnished the title compound (0.41 g) as white, hairy needles, mp 134°-136° C., Rf (ether): single spot, 0.6. By chromatography of the mother liquors and crystallization of the appropriate fractions, an additional 0.22 g of product, mp 138°-139° C., was obtained.

Workup

  1. washwashed with saturated NH4Cl solution twice
  2. dry with materialdried with magnesium sulfate
  3. customthe solvents evaporated under vacuum
  4. waitto stand overnight in 80% NeOH-H2O containing excess ammonium hydroxide
  5. washwashed with water, dilute KHSO4
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-a446c9d546444e85b5ed4da65c99e6af
Source dataset
uspto-grants-1995_04
Patent number
US05409925

Reaction notes

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