Diethyl Ether → HCID 20737861, compound

HRID 354272Notes

Reaction equation

HRID 354272 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24]C)=[O:23])[CH:18]=[CH:19][CH:20]=1)=[O:7])([CH3:4])(C)C.CCOCC.C([O-])(O)=O.[Na+].C(Cl)(OCC1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O.O.O1CCOCC1>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=1)([O:5][CH2:1][CH:4]1[C:45]2[C:46](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:47]2[C:52]1=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:7]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 86611298HCID 86611298, compound

Product 1

HCID 20737861HCID 20737861, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the above (S)-3-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxyphenyl acetic acid in CH2Cl2 (10 mL) and TFA (10 mL) was stirred for 1 hr at room temp. Et2O was added to the mixture and allowed to stand. Upper layer was removed by decantation to give an oil. A mixture of this oil in water (100 mL), dioxane (30 mL) and NaHCO3 (6.0 g) was added Fmoc-Cl (2.86 g, 11.1 mmol) and the mixture was stirred for 20 hr at room temp. The mixture was extracted with Et2O (×2), and the aqueous layer was acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc. The extract was washed with water, brine, dried over MgSO4 and concentrated in vacuo to afford 5.08 g (81%) (S)-3-(1-Fmoc-2-pyrrolidinyl)methoxyphenylacetic acid as a viscous oil.

Workup

  1. customUpper layer was removed by decantation
  2. customto give an oil
  3. stirringthe mixture was stirred for 20 hr at room temp
  4. extractionThe mixture was extracted with Et2O (×2)
  5. additionthe aqueous layer was acidified by the addition of 1 N HCl
  6. extractionThe mixture was extracted with EtOAc
  7. washThe extract was washed with water, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e471231832554200981a8854d2d8cc9f
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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