Hydrochloric Acid → HCID 68109219, compound

HRID 2179421Notes

Reaction equation

HRID 2179421 reaction equation
C([C:3]1([C:33]([O-:35])=[O:34])[C:8]2[C:9]3[CH:15]=[C:14]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:13]=[C:12]([Cl:25])[C:10]=3[O:11][C:7]=2[CH2:6][CH2:5][N:4]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])C.O.[OH-].[Li+].Cl>O.O1CCCC1>[C:29]([O:28][C:26]([N:4]1[CH2:5][CH2:6][C:7]2[O:11][C:10]3[C:12]([Cl:25])=[CH:13][C:14]([S:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)(=[O:17])=[O:18])=[CH:15][C:9]=3[C:8]=2[CH:3]1[C:33]([OH:35])=[O:34])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86668005HCID 86668005, compound

Product 1

HCID 68109219HCID 68109219, compoundYield 135.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Example 85, step C (80 mg, 0.12 mmol) in water (5 mL) and tetrahydrofuran (5 mL) was added lithium hydroxide monohydrate (84 mg, 2.0 mmol) at ambient temperature. After 2 h, 1 M HCl solution (3 mL) was added. The mixture was extracted with dichloromethane (2×10 mL) and the combined organic extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 2-(tert-butoxycarbonyl)-6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-1-carboxylic acid (80 mg, 99%) as a colorless oil which was used directly in the next step.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×10 mL)
  2. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-03dae176a37242d086ed6864976d46b3
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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