Cesium carbonate → HCID 89407762, compound

HRID 526313Notes

Reaction equation

HRID 526313 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:28][CH2:29][CH2:30]I>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:30][CH2:29][F:28])[CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 71258961HCID 71258961, compound

Product 1

HCID 89407762HCID 89407762, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3-[(tert-butoxycarbonyl)amino]-3-(3-hydroxyphenyl)propanoate (4.46 g, 20 mmol) in THF was added cesium carbonate (9.84 g, 30 mmol) and 1-fluoro-2-iodoethane (5 g, 30 mmol) and the mixture was stirred for 9 hours. After filtration the filtrate was concentrated in vacuum to yield 5.0 g of methyl 3-[(tert-butoxycarbonyl)amino]-3-[3-(2-fluoroethoxy)phenyl)propanoate.

Workup

  1. filtrationAfter filtration the filtrate
  2. concentrationwas concentrated in vacuum

Sources & evidence

ORD record
ord-aa2dd54df00e41f1b7928878ca8227aa
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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