Hydrochloric Acid → HCID 57208822, compound

HRID 1872464Notes

Reaction equation

HRID 1872464 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:23][CH2:24][CH:25]=[CH2:26])[C@@:10]2([NH2:22])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:5])C.O[Li].O.Cl>C1COCC1.O.CO>[CH2:24]([O:23][C@@H:9]1[CH2:8][C@@H:7]2[C@@H:11]([C@H:6]2[C:4]([OH:5])=[O:3])[C@:10]1([NH2:22])[C:12]([OH:14])=[O:13])[CH:25]=[CH2:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70075766HCID 70075766, compound

Product 1

HCID 57208822HCID 57208822, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (1S,2R,3R,5R,6S)-3-allyloxy-2-amino-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIV-2) (47 mg, 0.131 mmol) and LiOH.H2O (15 mg, 0.357 mmol) in THF (4 mL), H2O (2 mL) and MeOH (0.4 mL) was stirred at 23° C. for 36 h. The solution was acidified with conc. HCl and evaporated to dryness. The remaining pale yellow solid was suspended in EtOH, filtered, washed with more EtOH and the filtrate was evaporated to dryness. The residue was dissolved in EtOH (1 mL) and propylene oxide (1 mL) and refluxed for 3 min, whereupon the amino acid precipiated. After cooling to 23° C., the product was filtered off, washed with ether and dried to give (1S,2R,3R,5R,6S)-3-allyloxy-2-amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (I-9) (19 mg, 59%) as a white solid. 1H-NMR (250 MHz, D2O) □1.48 (1H, t, J=3.5 Hz), 1.78 (2H, m), 1.98 (1H, ddd, J=12.5, 8,3.5 Hz), 2.27 (1H, dd, J=12.5, 7 Hz), 3.44 (1H, bt, J=7.5 Hz), 3.97 (2H, m), 5.13-5.26 (2H, m), 5.82 (1H, ddt, J=18, 11, 6 Hz); MS[ISN] 240 [(M-H)- ]; mp>250° C.; ΞD20 -10.62° (c=0.40, H2O).

Workup

  1. customevaporated to dryness
  2. filtrationfiltered
  3. washwashed with more EtOH
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in EtOH (1 mL)
  6. temperaturepropylene oxide (1 mL) and refluxed for 3 min, whereupon the amino acid
  7. filtrationthe product was filtered off
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-4cc82034b6514be388c3dc022144d37c
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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