Hydrogen chloride-ethyl acetate → HCID 131736963, compound

HRID 58027Notes

Reaction equation

HRID 58027 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:29])[CH:16]([CH:25]([CH2:27][CH3:28])[CH3:26])[NH:17]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:31].[CH2:1]([O:8][C:9](=[O:30])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:29])[CH:16]([CH:25]([CH2:27][CH3:28])[CH3:26])[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131736964HCID 131736964, compound

Product 1

HCID 131736963HCID 131736963, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-t-butyloxycarbonyl-D,L-isoleucyl-L-proline benzyl ester (13 g) was dissolved in ethyl acetate (34 ml), and 15% HCl/ethyl acetate solution (25 ml) was added dropwisely upon cooled. After the completion of addition, the resulting mixture was allowed to warm up naturally to room temperature to react for 4 h, and then concentrated under reduced pressure to remove the reaction liquid, and the oil was recrystallized with isopropanol/n-hexane to give 4.5 g white solid (90%), with the content being 94% (HPLC, mobile phase 1, method 2).

Workup

  1. temperatureupon cooled
  2. additionAfter the completion of addition
  3. customto react for 4 h
  4. concentrationconcentrated under reduced pressure
  5. customto remove
  6. customthe reaction liquid
  7. customthe oil was recrystallized with isopropanol/n-hexane

Sources & evidence

ORD record
ord-b4309212a44f4971b334474eceb5a23e
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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