Hydrochloric Acid → HCID 59571129, compound

HRID 389214Notes

Reaction equation

HRID 389214 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:19][C@H:20]3[CH2:24][N:23]([C:25](=[O:43])[C@@H:26]([NH:34][C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[C@H:22]([C:44]([O:46]C)=[O:45])[CH2:21]3)=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[CH:48]=[CH2:49].[Li+].[OH-].Cl>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:19][C@H:20]3[CH2:24][N:23]([C:25](=[O:43])[C@@H:26]([NH:34][C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[C@H:22]([C:44]([OH:46])=[O:45])[CH2:21]3)=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[CH:48]=[CH2:49]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59571191HCID 59571191, compound

Product 1

HCID 59571129HCID 59571129, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Step 1 (0.68 g, 1.02 mmol) in THF (7 mL), MeOH (1 mL) and 1 M aqueous LiOH (7.15 mL, 7.15 mmol) was stirred at RT for 2 hours. The reaction mixture was acidified to pH 5 with 1 M aqueous HCl and extracted with EtOAc (3×70 mL). The combined organic phases were washed with water (50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated to give the title compound (0.56 g). LRMS (ESI) m/z 656.5 [(M+H)+; calcd for C38H46N3O7: 656.3].

Workup

  1. extractionextracted with EtOAc (3×70 mL)
  2. washThe combined organic phases were washed with water (50 mL), brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8afac3c99394126a68170a64c0f4b2f
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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