Water → HCID 118194618, compound

HRID 529283Notes

Reaction equation

HRID 529283 reaction equation
[CH2:1]([O:3][C:4]([O:23][CH2:24][CH3:25])([C@@H:10]([NH:14][C@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[CH2:11][CH2:12][CH3:13])[C:5]([O:7][CH2:8]C)=[O:6])[CH3:2].O.OS(O)(=O)=O>O(C(C)C)C(C)C>[CH2:24]([O:23][C:4]([O:3][CH2:1][CH3:2])([C@@H:10]([NH:14][C@H:15]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:16])[CH2:11][CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 118194606HCID 118194606, compound

Product 1

HCID 118194618HCID 118194618, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A diastereomeric mixture of (S)-ethyl 2,2-diethoxy-3-(((S)-1-phenylethyl)amino)hexanoate (6.4 g, d.r.: 85:15) was dissolved in 100 mL iPr2O and 2 mL water were added. The mixture was acidified to pH=2.21 with 50% H2SO4 and the resulting organic phase was concentrated to half its volume (50 mL). 1 mL water was added, and the mixture was acidified again to pH=2.22 with 50% H2SO4. The aqueous phase was combined with the aqueous phase from the previous extraction (V=1.5 mL) and extracted with 11 mL DIPET (diisopropyl ether) after adjusting the pH to 2.17 with 5M NaOH. The combined organic phases were concentrated (V=40 mL), 1 mL water was added and the mixture was acidified to pH=2.18 with 50% H2SO4. The organic phase was separated and the solvent was removed in vacuo to yield a 98:2 (syn:anti) mixture of diastereomers (37.5 mL solution, assay: 28%, 76% yield).

Workup

  1. concentrationthe resulting organic phase was concentrated to half its volume (50 mL)
  2. addition1 mL water was added
  3. extractionThe aqueous phase was combined with the aqueous phase from the previous extraction (V=1.5 mL)
  4. extractionextracted with 11 mL DIPET (diisopropyl ether)
  5. concentrationThe combined organic phases were concentrated (V=40 mL), 1 mL water
  6. additionwas added
  7. customThe organic phase was separated
  8. customthe solvent was removed in vacuo
  9. customto yield

Sources & evidence

ORD record
ord-0b603e7336664ead935d3ddaa09f6385
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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