Hydrochloric Acid → HCID 86653837, compound

HRID 925926Notes

Reaction equation

HRID 925926 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=3)[CH:13]=2)[CH2:7][C@H:6]1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])=[O:4].[Li+].[OH-].Cl>O.C1COCC1>[CH2:37]([O:36][C:34]([C@@H:6]1[CH2:7][C@H:8]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=3)[CH:13]=2)[CH2:9][CH2:10][C@H:5]1[C:3]([OH:4])=[O:2])=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67213544HCID 67213544, compound

Product 1

HCID 86653837HCID 86653837, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 34e (293 mg, 1 eq.) and LiOH (49 mg, 4 eq) in H2O (5 mL) and THF (5 mL) was stirred at room temperature for 4 hrs. The reaction mixture was acidified with 1N HCl to pH 2 and then extracted with DCM. Organics were concentrated under reduced pressure and purified by chromatography on silica gel (DCM/MeOH) to yield compound 34f as beige solid in 80% yield. MS (ESI, EI+): m/z=601 (MH+).

Workup

  1. extractionextracted with DCM
  2. concentrationOrganics were concentrated under reduced pressure
  3. custompurified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-0bc050239030403fabf302ae4c6eabcb
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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