Ammonium Hydroxide → HCID 10201900, compound

HRID 842108Notes

Reaction equation

HRID 842108 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH:13]1([O:18][C:19]2[CH:20]=[C:21]([CH:37]=[CH:38][C:39]=2[O:40][CH3:41])[CH2:22][C:23]2[O:24][C:25]3[C:31]([CH2:32][C:33]([OH:35])=O)=[CH:30][C:29]([Cl:36])=[CH:28][C:26]=3[N:27]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[NH4+].[OH-]>O1CCCC1>[CH:13]1([O:18][C:19]2[CH:20]=[C:21]([CH:37]=[CH:38][C:39]=2[O:40][CH3:41])[CH2:22][C:23]2[O:24][C:25]3[C:31]([CH2:32][C:33]([NH2:3])=[O:35])=[CH:30][C:29]([Cl:36])=[CH:28][C:26]=3[N:27]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 10273345HCID 10273345, compound

Product 1

HCID 10201900HCID 10201900, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1′-carbonyl diimidazole (0.31 g, 0.0019 mol) was dissolved in 15 ml of tetrahydrofuran and 2-(3-cyclopentyloxy-4-methoxybenzyl)-5-chlorobenzoxazole-7-acetic acid (1.14 g, 0.0027 mol) was added in a tetrahydrofuran (THF) solution. After stirring for 1 hour, the reaction mixture was treated with 2 ml of concentrated NH4OH and stirred a further 3.5 hours. The tetrahydrofuran was removed under reduced pressure and the remaining material was extracted with CH2Cl2. The organic layer was separated and washed with 50 ml of CH2Cl2. A crystalline solid (0.6 g) was isolated after drying and evaporating the CH2Cl2. The solid was recrystallized from 20 ml of CH3OH to yield 0.3 g of title compound, mp 162-164° C.

Workup

  1. stirringstirred a further 3.5 hours
  2. customThe tetrahydrofuran was removed under reduced pressure
  3. extractionthe remaining material was extracted with CH2Cl2
  4. customThe organic layer was separated
  5. washwashed with 50 ml of CH2Cl2

Sources & evidence

ORD record
ord-2aec98cbb155435fb7166436aa9d368d
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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