Diisopropyl Ether → HCID 86706788, compound

HRID 1848770Notes

Reaction equation

HRID 1848770 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.[NH2:15][C@@H:16]([CH3:31])[C:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].C(OC(C)C)(C)C>C(OCC)(=O)C>[NH2:15][C@@H:16]([CH3:31])[C:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 681926(2S)-2-Amino-1,1-diphenylpropan-1-olHCID 21109152-(6-Hydroxy-1-benzofuran-3-yl)acetic acid

Product 1

HCID 86706788HCID 86706788, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(6-Hydroxy-1-benzofuran-3-yl)acetic acid (25.00 g) and (S)-2-amino-1,1-diphenylpropan-1-ol (29.57 g) were added to ethyl acetate (175 mL), and the mixture was dissolved by stirring at 60° C. After allowing to cool to room temperature, isopropyl ether (200 mL) was added, and the mixture was stirred for 1 hr. The solid was collected by filtration, and washed with a mixed solvent (1:1, 100 mL) of ethyl acetate-isopropyl ether. The solid was dried under reduced pressure at 50° C. to give the title compound (53.81 g).

Workup

  1. dissolutionthe mixture was dissolved
  2. temperatureto cool to room temperature
  3. stirringthe mixture was stirred for 1 hr
  4. filtrationThe solid was collected by filtration
  5. washwashed with a mixed solvent (1:1, 100 mL) of ethyl acetate-isopropyl ether
  6. customThe solid was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-36126c47527c46ce8872b037f179c158
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

Loading…