Hydrochloric Acid → HCID 14986688, compound

HRID 465589Notes

Reaction equation

HRID 465589 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28][O:29]C2CCCCO2)[CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14986687HCID 14986687, compound

Product 1

HCID 14986688HCID 14986688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.453 g of t-butyl 8-(p-chlorophenylsulfonamido)-4-[3-(tetrahydropyranyloxy)propyl]-octanoate in 7 ml tetrahydrofuran is added 5 ml of 1N hydrochloric acid and the solution is allowed to stir for 18 h. The reaction mixture is diluted with water and extracted with ethyl acetate to give a yellow oil which is chromatographed on silica gel using ethyl acetate/hexane (1:4) as eluent to yield t-butyl 8-(p-chlorophenylsulfonamido)-4-(3-hydroxypropyl)-octanoate; NMR (CDCl3): delta 3.65 (m,2H), 3.0 (q,2H), 2.2 (t,2H).

Workup

  1. extractionextracted with ethyl acetate
  2. customto give a yellow oil which
  3. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-19f2807a66ac43229020121da1633008
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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