Diisopropylcarbodiimide → 2-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester

HRID 914387Notes

Reaction equation

HRID 914387 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:21]1[C:33]2[CH:32]([CH2:34]O)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1.C(N=C=NC(C)C)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([O:19][CH2:34][CH:32]2[C:33]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 904669H-Fluorene-9-methanolHCID 59759443{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid

Product 1

HCID 597593352-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl esterYield 105%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[(2-tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid (160 g) obtained in Example 3 in dichloromethane (500 mL) were added 9H-fluorene-9-ylmethanol (98 g) and 4-dimethylaminopyridine (3.1 g), diisopropylcarbodiimide (78 ml) was added dropwise under ice-cooling, and the mixture was stirred at 0° C. for 1 hr and further stirred at room temperature for 2 hr. The precipitate was removed from the reaction mixture by filtration, and the filtrate was concentrated under reduced pressure and purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (260 g) as a yellow oil.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. stirringfurther stirred at room temperature for 2 hr
  4. customThe precipitate was removed from the reaction mixture by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. custompurified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8aadb8aab26a491a983014d15b088186
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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