Sodium Hydroxide → HCID 11584814, compound

HRID 1099324Notes

Reaction equation

HRID 1099324 reaction equation
C([O:3][C:4](=[O:52])[C@@H:5]([CH:49]([CH3:51])[CH3:50])[C:6](C(OCC)=O)(C(OCCC)=O)[C:7](=[O:37])[C@@H:8]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)[CH:11]([CH3:13])[CH3:12])C.[OH-].[Na+]>C(O)C>[C:33]([O:32][C:30]([NH:29][C@@H:8]([CH2:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)[CH:11]([CH3:12])[CH3:13])[C:7](=[O:37])[CH2:6][C@@H:5]([CH:49]([CH3:50])[CH3:51])[C:4]([OH:52])=[O:3])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66813952HCID 66813952, compound

Product 1

HCID 11584814HCID 11584814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g of (2S,5S,7S)-5-tert-butoxycarbonylamino-3-ethoxycarbonyl-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-8-methyl-4-oxo-3-propoxycarbonyl-nonanoic acid ethyl ester in 20 mL of ethanol is treated with 25 mL of a 37% solution of sodium hydroxide at room temperature. The reaction mixture is stirred for 24 hours at room temperature and the ethanol removed by distillation in vacuum. The residue is extracted twice with 25 mL of dichloromethane. The pH of the aqueous layer is carefully adjusted to 2.5 with 2 N hydrochloric acid at 0° C., the reaction mixture is then stirred for 16 hours and extracted 4 times with 50 mL of dichloromethane. The organic layer is dried and the solvent removed to give the title compound as an oil.

Workup

  1. customthe ethanol removed by distillation in vacuum
  2. extractionThe residue is extracted twice with 25 mL of dichloromethane
  3. customis carefully adjusted to 2.5 with 2 N hydrochloric acid at 0° C.
  4. stirringthe reaction mixture is then stirred for 16 hours
  5. extractionextracted 4 times with 50 mL of dichloromethane
  6. customThe organic layer is dried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-4e2eb09206d7475e9aa93eb83a25705c
Source dataset
uspto-grants-2012_03
Patent number
US08143416B2

Reaction notes

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