Lithium Hydroxide → 5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,4-dimethoxyphenyl)methyl]hexanoic acid

HRID 2394143Notes

Reaction equation

HRID 2394143 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]=CC(OC)=[CH:26][C:25]=2[O:32][CH3:33])[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:2].[Li+].[OH-:35].CO[CH2:38][CH2:39][O:40][CH3:41]>O.C(OCC)(=O)C>[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:35])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:38][C:39]([O:40][CH3:41])=[CH:26][C:25]=1[O:32][CH3:33])[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 701496735(S)-[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(2,4-dimethoxyphenyl)methyl]-dihydrofuran-2-(3H)-one

Product 1

HCID 228764045(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,4-dimethoxyphenyl)methyl]hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.58 g (3.47 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,4-dimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 56 ml of ethylene glycol dimethyl ether and 28.2 ml of water is treated, at RT, with 13.87 ml of a 1M solution of LiOH in water, and this mixture is stirred for 1.75 h. After that, the reaction mixture is diluted with ethyl acetate and a little THF and the whole is washed firstly with a mixture consisting of 170.6 ml of sat. ammonium chloride solution and 14.25 ml of 10% citric acid solution (both being cold) and then with saline. The combined aqueous phases are reextracted with ethyl acetate. The combined organic phases are dried over Na2 SO4 and evaporated on a RE at about 30° C. The residue, which is the title compound, is triturated with hexane and filtered off with suction. M.p.: 144-145 C.-TLC Rf (D)=at the start.-FAB-MS (M+H)+ =474.-HPLC tRet =14.34 min (gradient II).-IR(KBr)=u.a. 3420, 3350, 2818, 1686, 1518 and 1508 cm-1.-1H-NMR(CD3OD)=inter alia 7.30-7.09/m (5H); 6.94/d (1H); 6.47/d (1H); 6.37/d×d (1H); 3,78 and 3.75/each s (each 3H); 1.33/s (9H).

Workup

  1. washa little THF and the whole is washed firstly with a mixture
  2. customThe combined organic phases are dried over Na2 SO4
  3. customevaporated on a RE at about 30° C
  4. customis triturated with hexane
  5. filtrationfiltered off with suction
  6. customat the start.-FAB-MS (M+H)+ =474.-HPLC tRet =14.34 min (gradient II)

Sources & evidence

ORD record
ord-b4fe13b3829748f696e99cc911e91633
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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