Hydrochloric Acid → HCID 118204374, compound

HRID 529288Notes

Reaction equation

HRID 529288 reaction equation
C(OC(N[C@@H](CCC)C(OC)(OC)C(O)=O)=O)(C)(C)C.[OH-].[K+].[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:44][CH2:45][CH3:46])[C:32]([O:41][CH2:42][CH3:43])([O:38][CH2:39][CH3:40])[C:33]([O:35]CC)=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24].Cl>O.CCO.ClCCl>[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:44][CH2:45][CH3:46])[C:32]([O:38][CH2:39][CH3:40])([O:41][CH2:42][CH3:43])[C:33]([OH:35])=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 118194600HCID 118194600, compoundHCID 118194611HCID 118194611, compound

Product 1

HCID 118204374HCID 118204374, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Step 2—preparation of (S)-3-(tert-butoxycarbonylamino)-2,2-dimethoxyhexanoic acid: A solution of KOH (6.95 g, 123.9 mmol) in 100 mL water was added to a solution of Ethyl(S)-3-(tert-butoxycarbonylamino)-2,2-diethoxyhexanoate (8.6 g, 24.6 mmol) in 100 mL EtOH. Further 100 mL EtOH were added to obtain a clear solution and the mixture was stirred at room temperature for 23 hours. Dichloromethane (200 mL) and water (200 mL) were added, and the pH of the mixture was adjusted with conc. HCl from 12.5 to 2.5. The phases were separated, and the aqueous phase was extracted twice with dichloromethane (100 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed in vacuo to yield 6.3 g (S)-3-(tert-butoxycarbonylamino)-2,2-diethoxyhexanoic acid (80% yield).

Workup

  1. customto obtain a clear solution
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with dichloromethane (100 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fab2fd972766487a8a4377433bd250d0
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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