Hydrochloric Acid → HCID 59571253, compound

HRID 389215Notes

Reaction equation

HRID 389215 reaction equation
[CH3:1][C:2]([CH3:51])([CH2:48][CH:49]=[CH2:50])[CH2:3][O:4][C:5]([NH:7][C@@H:8]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH2:47])[C:9]([N:11]1[CH2:19][C@H:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([CH:31]=[CH2:32])[CH:29]=3)[N:24]=[C:23]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:22]=2)[CH2:17][C@H:12]1[C:13]([O:15]C)=[O:14])=[O:10])=[O:6].Cl>C1COCC1.CO.[Li+].[OH-]>[CH3:1][C:2]([CH3:51])([CH2:48][CH:49]=[CH2:50])[CH2:3][O:4][C:5]([NH:7][C@@H:8]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH2:47])[C:9]([N:11]1[CH2:19][C@H:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([CH:31]=[CH2:32])[CH:29]=3)[N:24]=[C:23]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:22]=2)[CH2:17][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])=[O:6]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59571245HCID 59571245, compound

Product 1

HCID 59571253HCID 59571253, compoundYield 89.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Step 1 (962 mg, 1.38 mmol) in THF (10 mL), MeOH (1 mL) and 1 M aqueous LiOH (9.65 mL) was stirred at RT for 2 hours. The reaction solution was acidified to pH 5 with 1 M aqueous HCl and extracted with EtOAc (3×100 mL). The combined EtOAc layers were washed with water (50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated to give the title product (844 mg). LRMS (ESI) m/z 684.5 [(M+H)+; calcd for C40H50N3O7: 684.4].

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined EtOAc layers were washed with water (50 mL), brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c24decbd94f4362911889c9914e095d
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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