Acetonitrile → 4-(4-S-Acetyl-2,5-anhydro-3-deoxy-4-thio-L-threo-pentonoyl)-1-Piperazinecarboxylic acid phenylmethyl ester

HRID 1290401Notes

Reaction equation

HRID 1290401 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C@@H:19]3[O:23][CH2:22][C@@H:21](Br)[CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]([O-:28])(=[S:27])[CH3:26].[K+].C1OCCOCCOCCOCCOCCOC1.C(#N)C>C(OCC)(=O)C.CCCCCC>[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C@@H:19]3[O:23][CH2:22][C@H:21]([S:27][C:25](=[O:28])[CH3:26])[CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2855718-Crown-6HCID 23670855Potassium ethanethioateHCID 1317198554-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester

Product 1

HCID 1317198564-(4-S-Acetyl-2,5-anhydro-3-deoxy-4-thio-L-threo-pentonoyl)-1-Piperazinecarboxylic acid phenylmethyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound is prepared by the procedure of Example 139 using 1.14 g of product from Example 151, 0.393 g of potassium thioacetate, 0.1517 g of 18-crown-6 and 10 ml of acetonitrile to give 0.928 g of the desired product after chromatography (silica gel: 10-60% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-214ec7756069459c9ffb45b0e505e08e
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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