Lithium Hydroxide → HCID 22876406, compound

HRID 1377205Notes

Reaction equation

HRID 1377205 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][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[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-:36].[Li+].C(COC)[O:39]C>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:39])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:26][CH:25]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:36]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 70150892HCID 70150892, compound

Product 1

HCID 22876406HCID 22876406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.3 g (2.76 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(4-biphenylyl)methyl]dihydrofuran-2-(3H)-one are hydrolysed, in 28 ml of dimethoxyethane, with 11 ml of a 1M solution of lithium hydroxide in water. After 16 h at PT, the dimethoxyethane is evaporated off on a RE and the residue is treated with an ice-cold mixture of 15 ml of sat. NH4Cl solution, 80 ml of 10% citric acid solution and methylene chloride. The aqueous phase is separated off and extracted 2× with methylene chloride. The organic phases are washed with saline, dried with Na2SO4 and evaporated to give the title compound: TLC Rf (B)=0.4; tRet (II)=16.4 min.

Workup

  1. customthe dimethoxyethane is evaporated off on a RE and the residue
  2. additionis treated with an ice-cold mixture of 15 ml of sat. NH4Cl solution, 80 ml of 10% citric acid solution and methylene chloride
  3. customThe aqueous phase is separated off
  4. extractionextracted 2× with methylene chloride
  5. washThe organic phases are washed with saline
  6. dry with materialdried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-efbd1656673740ca99161e18da9c408b
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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