Hydrochloric Acid → HCID 58360480, compound

HRID 626644Notes

Reaction equation

HRID 626644 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:29][CH:28]=1)[C:10]([NH:12][C@@H:13]([CH:23]([CH3:25])[CH3:24])[CH2:14][O:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:10]([NH:12][C@@H:13]([CH:23]([CH3:25])[CH3:24])[CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:11])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67028421HCID 67028421, compound

Product 1

HCID 58360480HCID 58360480, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

355.0 mg (0.52 mmol) of ethyl 3-((S)-2-{(R)-2-tert-butoxycarbonylamino-3-[4-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]propionylamino}-3-methylbutoxy)propionate were dissolved in a mixture of 9 ml of THF and 3 ml of MeOH. 1.29 ml (1.29 mmol) of an aqueous 1M LiOH solution were added, and the resulting reaction mixture was stirred at room temp. for 1 h. After the reaction was complete, the mixture was neutralized by adding a little aqueous 1N HCl solution, concentrated under reduced pressure and codistilled with toluene. The product obtained in this way (225.0 mg) was employed crude in the next reaction.

Workup

  1. customthe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. customThe product obtained in this way (225.0 mg)
  4. customin the next reaction

Sources & evidence

ORD record
ord-1c06db8a32204e89a8516391f16ca81d
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Reaction notes

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