Hydrochloric Acid → HCID 67045964, compound

HRID 606548Notes

Reaction equation

HRID 606548 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:32])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:20]=1)(=[O:16])=[O:15])C.Cl>O.C1COCC1>[OH:31][CH:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][S:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:32])=[O:5])(=[O:16])=[O:15])=[CH:20][CH:21]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 670459707-[[4-(1-Hydroxyhexyl)benzyl]methanesulfonylamino]heptanoic Acid Ethyl Ester

Product 1

HCID 67045964HCID 67045964, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.47 mL of a 0.5 N solution in H2O, 0.236 mmol) was added to a solution of the ester 11 (52 mg, 0.118 mmol) in THF (1.5 mL) at 23° C. The reaction mixture was stirred for 16 h, acidified with 1 N HCl and extracted with EtOAc. The organic portion was washed with brine (2×), dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 100% EtOAc) gave 36.2 mg (72%) of the free acid 12 as a light yellow, viscous oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfc8e21672784b329b0c03b3a6f2dab3
Source dataset
uspto-grants-2011_03
Patent number
US07915316B2

Reaction notes

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