Hydrochloric Acid → (1S,2S,5R,6S)-2-[[(2S)-2-aminopropanoyl]amino]spiro[bicyclo[3.1.0]hexane-4,1'-cyclopropane]-2,6-dicarboxylic acid

HRID 2037294Notes

Reaction equation

HRID 2037294 reaction equation
Cl.C(OC([NH:9][C@@H:10]([CH3:28])[C:11]([NH:13][C@@:14]1([C:25]([OH:27])=[O:26])[CH2:21][C:18]2([CH2:20][CH2:19]2)[C@@H:17]2[C@H:15]1[C@H:16]2[C:22]([OH:24])=[O:23])=[O:12])=O)(C)(C)C.[OH-].[Na+]>CC(C)=O.O>[NH2:9][C@@H:10]([CH3:28])[C:11]([NH:13][C@@:14]1([C:25]([OH:27])=[O:26])[CH2:21][C:18]2([CH2:19][CH2:20]2)[C@@H:17]2[C@H:15]1[C@H:16]2[C:22]([OH:24])=[O:23])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86691269(1S,2S,5R,6S)-2-[[(2S)-2-(tert-butoxy carbonylamino)propanoyl]amino]spiro[bicyclo[3.1.0]hexane-4,1'-cyclopropane]-2,6-dicarboxylic acid

Product 1

HCID 71655813(1S,2S,5R,6S)-2-[[(2S)-2-aminopropanoyl]amino]spiro[bicyclo[3.1.0]hexane-4,1'-cyclopropane]-2,6-dicarboxylic acidYield 59.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Add concentrated hydrochloric acid (36.94 mL, 430.11 mmol) to a solution of (1S,2S,5R,6S)-2-[[(2S)-2-(tert-butoxycarbonylamino)propanoyl]amino]spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylic acid (82.24 g, 215.06 mmol) in acetone (822.4 mL), and stir the mixture at 50° C. After 1.5 hours cool the mixture to 0° C. and add 50% sodium hydroxide in water to pH=3.6-3.8. Stir the solid obtained for 1 hour, filter and wash with water. Dry under vacuum for 48 hours to yield the title compound as a white solid (36 g, 127.53 mmol). MS (m/z): 283 (M+1).

Workup

  1. temperatureAfter 1.5 hours cool the mixture to 0° C.
  2. stirringStir the solid
  3. customobtained for 1 hour
  4. filtrationfilter
  5. washwash with water
  6. customDry under vacuum for 48 hours

Sources & evidence

ORD record
ord-f02d14f1bfbd400ca38b50fb4bd8d5ab
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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