Hydrochloric Acid → HCID 10934012, compound

HRID 1040660Notes

Reaction equation

HRID 1040660 reaction equation
C1([C@H](N)C)C=CC=CC=1.[C:10]([O:14][C:15]([NH:17][C@@H:18]1[C@@H:23]2[CH2:24][C@@H:20]([CH:21]=[CH:22]2)[C@@H:19]1[C:25]([OH:27])=[O:26])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(OCC)(=O)C.Cl>O>[C:10]([O:14][C:15]([NH:17][C@@H:18]1[C@@H:23]2[CH2:24][C@@H:20]([CH:21]=[CH:22]2)[C@@H:19]1[C:25]([OH:27])=[O:26])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67264621HCID 67264621, compound

Product 1

HCID 10934012HCID 10934012, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(1S,2S,3R,4R)-3-tert-Butoxycarbonylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (R)-1-phenyl-ethylamine salt (10.0 g, 26.7 mmol) in Ethyl acetate (200 mL, 2000 mmol;) and Water (100 mL, 6000 mmol;) was added 1 M of Hydrogen Chloride in Water (50 mL) via pipette to pH 2. The layers were separated and the aqueous was extracted (EtOAc), drying of combined organics (MgSO4) provided (1S,2S,3R,4R)-3-tert-Butoxycarbonylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid as a white foamy solid 6.74 grams 1H-NMR (CDCL3, 400 MHz): δ 12.30 (broad peak 1H) m 6.99 (d, J=9.6 Hz, 1H), 6.20 (vroad s, 2H), 3.97 (t, J=9.6 Hz, 1H), 3.05 (s, 1H), 2.74 (s, 1H), 2.60 (d, J=8.4 Hz, 1H), 2.09 (d, J=9.6 Hz, 1H), 1.66 (d, J=9.6 Hz, 1H), 1.46 (s, 9H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted (EtOAc)
  3. dry with materialdrying of combined organics (MgSO4)

Sources & evidence

ORD record
ord-4d54a74dec744d4da6c03f159a53a4eb
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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