Water → HCID 49833752, compound

HRID 1614864Notes

Reaction equation

HRID 1614864 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13](O)=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.C1N=C[N:20](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+].O>CN(C=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([NH2:20])=[O:14])=[CH:9][CH:8]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 49834134HCID 49834134, compound

Product 1

HCID 49833752HCID 49833752, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (1.6 mmol, 375 mg) was dissolved in DMF (3 mL), then CDI (1.84 mmol, 299 mg) was added and the reaction mixture stirred at r.t. for 90 min. Ammonium hydroxide (25% aq, 7 mL) was added and a precipitate formed. Water (7 mL) was added and the precipitate filtered off and dried in vacuo to yield the title compound (302 mg, 81%). 1H NMR (300 MHz, CDCl3) δ 7.25-7.14 (m, 2H), 6.97-6.83 (m, 2H), 6.78 (bs, 1H), 5.91 (bs, 1H), 4.49 (s, 2H), 3.52-3.28 (m, 1H), 2.77-2.57 (m, 1H), 2.57-2.11 (m, 5H), 2.09-1.79 (m, 1H).

Workup

  1. customa precipitate formed
  2. filtrationthe precipitate filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1415293e8d88416fb053ee83379b3393
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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