Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

HRID 2394117Notes

Reaction equation

HRID 2394117 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[OH-:30].[Li+].C[O:33]CCOC>O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20]([OH:22])=[O:33])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:30]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 117320045(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one

Product 1

HCID 99791245(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 17.6 g of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one in 710 ml of ethylene glycol dimethyl ether and 352 ml of water is treated dropwise, at 20° C. and within the space of 10 min, with 176 ml of a 1M lithium hydroxide solution. After that, the reaction mixture is stirred at RT for 1.5 h, and the solvent is then evaporated off. The residue is poured onto 1 l of cold 10% citric acid, and this acidic solution is extracted three times with 800 ml of ethyl acetate on each occasion. The combined extracts are washed first with 800 ml of water and then with 800 ml of saline. After the organic solution has been dried over sodium sulfate, the solvent is distilled off. The crude title compound is employed in the next stage without any further purification. FAB-MS (M+H)+ =414.

Workup

  1. customthe solvent is then evaporated off
  2. additionThe residue is poured onto 1 l of cold 10% citric acid
  3. extractionthis acidic solution is extracted three times with 800 ml of ethyl acetate on each occasion
  4. washThe combined extracts are washed first with 800 ml of water
  5. dry with materialAfter the organic solution has been dried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe crude title compound is employed in the next stage without any further purification

Sources & evidence

ORD record
ord-bc2c8ba8406b45be9b8314ec183b24c4
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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