Hydrochloric Acid → HCID 21224234, compound

HRID 1584405Notes

Reaction equation

HRID 1584405 reaction equation
C([O:5][NH:6][C:7](=[O:37])[CH2:8][C:9]1([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)(C)(C)C.Cl>ClC(Cl)C>[OH:5][NH:6][C:7](=[O:37])[CH2:8][C:9]1([S:21]([C:24]2[CH:25]=[CH:26][C:27]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH2:10][CH2:11][N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21224255HCID 21224255, compound

Product 1

HCID 21224234HCID 21224234, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 20A, N-tert-butoxy-2-[4-(4-phenoxyphenylsulfonyl)-1-(ethoxycarbonylmethyl)piperidin-4-yl]-acetamide, was dissolved in dichloroethane (10 ml), cooled to 0° C., and saturated with hydrochloric acid gas. The reaction vessel was then sealed and the solution stirred for two days at 25° C. Solvent was removed from the reaction mixture under reduced pressure, and the residue purified by preparative TLC, eluting with 10% methanol/methylene chloride, to give N-hydroxy-2-[4-(4-phenoxyphenylsulfonyl)-1-(ethoxycarbonylmethyl)piperidin-4-yl]-acetamide (420 mg), m/e=477.1 (MH+, FABMS).

Workup

  1. customThe reaction vessel was then sealed
  2. customSolvent was removed from the reaction mixture under reduced pressure
  3. customthe residue purified by preparative TLC
  4. washeluting with 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-85c4759cccad4db98a4a93c69b636b83
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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