Hydrochloric Acid → HCID 57064308, compound

HRID 1872468Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH:8]=[CH:9][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])[CH:9]=[CH:8][C@@H:7]2[C@H:11]1[C@H:6]2[C:4]([OH:5])=[O:3]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of (1S,2R,5R,6S)-2-amino-bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXVII) (19 mg, 0.063 mmol) and LiOH.H2O (8 mg, 0.19 mmol) in THF (2 mL), H2O (0.5 mL) and MeOH (0.2 mL) was stirred at 23° C. for 10 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,5R,6S)-2-amino-bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylic acid (I-10) (11 mg, 95%) as a white solid. 1H-NMR (250 MHz, D2O) □1.59 (1H, t,J=3 Hz), 2.32 (1H, m), 2.60 (1H, m), 5.44 (1H, d, J=5.5 Hz), 6.37 (1H, dd,J=5.5, 2 Hz); MS[ISN] 182 [(M-H)- ]; mp>250° C.;

Workup

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

Sources & evidence

ORD record: ord-4e7ce3db1089488b9d6aae958226d588
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107342

Reaction notes

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