Sodium Hydroxide → HCID 131719857, compound

HRID 54791Notes

Reaction equation

HRID 54791 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:27][CH2:26][C@H:21]([S:22]C(=O)C)[CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[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:27][CH2:26][C@H:21]([SH:22])[CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 1317198564-(4-S-Acetyl-2,5-anhydro-3-deoxy-4-thio-L-threo-pentonoyl)-1-Piperazinecarboxylic acid phenylmethyl ester

Product 1

HCID 131719857HCID 131719857, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 0° C. solution, under argon, of 0.20 g of product from Example 152 in 1.5 ml of dry methyl alcohol is treated with 0.25 ml of 4N sodium hydroxide. The reaction is monitored by thin layer chromatography. After 1 hour an additional 0.17 ml of 4N sodium hydroxide is added and the reaction stirred 1 hour. The reaction mixture is quenched with 1.86N hydrochloric acid/isopropyl alcohol, concentrated in vacuo and chromatographed (silica gel: 20-80% ethyl acetate/hexane) to give 0.116 g of the desired product.

Workup

  1. customThe reaction mixture is quenched with 1.86N hydrochloric acid/isopropyl alcohol
  2. concentrationconcentrated in vacuo
  3. customchromatographed (silica gel: 20-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d72233d1991f4ec9845beb7094d7c1db
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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