Lithium Hydroxide → HCID 22876408, compound

HRID 2394096Notes

Reaction equation

HRID 2394096 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]([CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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:2].[OH-:38].[Li+]>C(COC)OC.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:38])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:29]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70150597HCID 70150597, compound

Product 1

HCID 22876408HCID 22876408, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5.15 g (10.31 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-{[p-(2-phenylethyl)phenyl]methyl}dihydrofuran-2-(3H)-one in 166 ml of dimethoxyethane and 85 ml of water are hydrolysed, under protective gas, with 41 ml of a 1M lithium hydroxide solution. After 3 h, the dimethoxyethane is evaporated off on an RE, and the residue is treated with an ice-cold mixture of 506 ml of sat. NH4Cl solution, 42 ml of 10% citric acid solution and 207 ml of methylene chloride. Methanol is added to dissolve the product completely. The aqueous phase is separated off and extracted 2× with methylene chloride/methanol, 10:1. The organic phases are washed with saline, dried with Na2SO4 and evaporated: tRet (II)=17.8 min.

Workup

  1. customthe dimethoxyethane is evaporated off on an RE, and the residue
  2. additionis treated with an ice-cold mixture of 506 ml of sat. NH4Cl solution, 42 ml of 10% citric acid solution and 207 ml of methylene chloride
  3. additionMethanol is added
  4. dissolutionto dissolve the product completely
  5. customThe aqueous phase is separated off
  6. extractionextracted 2× with methylene chloride/methanol, 10:1
  7. washThe organic phases are washed with saline
  8. dry with materialdried with Na2SO4
  9. customevaporated
  10. customtRet (II)=17.8 min.

Sources & evidence

ORD record
ord-75ccffe871af4f489b0fc8068c1f0856
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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