Hydrochloric Acid → HCID 57225017, compound

HRID 1872465Notes

Reaction equation

HRID 1872465 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][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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>[NH2:22][C@@:10]1([C:12]([OH:14])=[O:13])[C@H:9]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][C@@H:7]2[C@H:11]1[C@H:6]2[C:4]([OH:5])=[O:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70076632HCID 70076632, compound

Product 1

HCID 57225017HCID 57225017, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (1S,2R,3R,5R,6S)-2-amino-3-benzyloxy-bicyclo [3.1.0] hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIV-3) (50 mg, 0.122 mmol) and LiOH.H2O (13 mg, 0.30 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)-2-amino-3-benzyloxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid (I-10) (26 mg, 72%) as a white solid. 1H-NMR (250 MHz, D2O) □1.57 (1H, t, J=3.5 Hz), 1.97 (2H, m), 2.13 (1H, ddd, J=12.5, 8,3.5 Hz), 2.35 (1H, dd, J=12.5, 7 Hz), 3.73 (1H, dd, J=8, 7 Hz), 4.51 (2H, s), 7.36 (5H, bm); MS[ISN] 290 [(M-H)- ]; mp>250° C.; □D20 -5.69° (c=0.25, 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-94b47de4e41e4d628eba55b10c7d3e9c
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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