Hydrochloric Acid → HCID 69055271, compound

HRID 2100625Notes

Reaction equation

HRID 2100625 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2].Cl>C(OCC)C>[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:17][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69056703HCID 69056703, compound

Product 1

HCID 69055271HCID 69055271, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3aR,9bS)-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Part B above, (48 mg, 0.15 mmol) in 2 mL of diethyl ether was added 1 mL of 12 N HCl. The resulting mixture was stirred vigorously for 5 min at ambient temperature and then was concentrated and dried in vacuo. The resulting white solid was triturated twice with diethyl ether and dried in vacuo. The residue was dissolved in 1 mL distilled water, filtered, and lyophilized to afford 30 mg (79%) of the title compound of Example 74 as a white powder. 1H NMR (DMSO-d6): δ 9.40 (broad s, 2H), 8.47 (s, 1H), 7.07 (s, 1H), 6.89 (s, 1H), 3.87-3.82 (m, 1H), 3.52-3.46 (m, 1H), 3.45-3.40 (m, 1H), 3.21-3.10 (overlapping m, 2H), 3.07-3.01 (m, 1H), 2.58 (q, 2H, J=7.5 Hz), 2.54 (s, 3H), 1.18 (t, 3H, J=7.7 Hz). LRMS (ESI): 231.2 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customdried in vacuo
  3. customThe resulting white solid was triturated twice with diethyl ether
  4. customdried in vacuo
  5. dissolutionThe residue was dissolved in 1 mL
  6. distillationdistilled water
  7. filtrationfiltered

Sources & evidence

ORD record
ord-28a4498ed7b2431ba86f05f3b329ee87
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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