HCID 67499481, compound → HCID 86628917, compound

HRID 1919448Notes

Reaction equation

HRID 1919448 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:15]([OH:17])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2].[C:28]1([CH2:34][O:35][CH2:36][C:37]([O:39][CH:40](Cl)[CH3:41])=[O:38])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:15]([O:17][CH2:41][CH2:40][O:39][C:37](=[O:38])[CH2:36][O:35][CH2:34][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67499481HCID 67499481, compoundHCID 86628882HCID 86628882, compound

Product 1

HCID 86628917HCID 86628917, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoic acid (17) (0.8 g, 2.0 mmol) dissolved in 12 mL of anhydrous toluene was reacted with 1.4 g (6.0 mmol) of 1-chloroethyl 2-(phenylmethoxy)acetate (25) in the presence of 1.1 g (4.0 mmol) of silver carbonate (Ag2CO3). After work-up and further purification by mass-guided preparative HPLC, 0.1 g (8.4% yield) of the title compound (45a) was obtained as a colorless, viscous oil. MS (ESI) m/z 594.15 (M+H)+, 616.20 (M+Na)+.

Workup

  1. customAfter work-up and further purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-dc168a13d5564086a7ebeb931002c3d5
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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