Methanol → H-alpha-Me-D-Phe(3-I)-OH

HRID 857118Notes

Reaction equation

HRID 857118 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][C@:6]1([CH3:28])[C:10](=[O:11])[O:9][C@@H](C2C=CC=CC=2)[N:7]1C(OCC1C=CC=CC=1)=O.C[Si](C)(C)[O-].[K+].CO>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][C@:6]([CH3:28])([C:10]([OH:11])=[O:9])[NH2:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 11827521HCID 11827521, compoundHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 10357711H-alpha-Me-D-Phe(3-I)-OHYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of benzyl (2S,4R)-4-(3-iodobenzyl)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate (1.47 g) and potassium trimethylsilanolate (1.2 g) was suspended in THF (50 ml) and heated to 75° C. for 2.5 h. MeOH (10 ml) was added and the solvents were removed under reduced pressure. The residue was dissolved in MeOH and applied to two 10 g SCX-2 cartridges eluting with MeOH and then with 0.2M ammonia in MeOH. The ammoniacal solutions were evaporated to dryness to give the title compound (910 mg) LCMS RT=1.93 min.

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in MeOH
  3. washeluting with MeOH
  4. customThe ammoniacal solutions were evaporated to dryness

Sources & evidence

ORD record
ord-e514dc7a34134366a379363782f8100d
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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