Hydrochloric Acid → HCID 11673444, compound

HRID 2100613Notes

Reaction equation

HRID 2100613 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([F:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2].[ClH:25]>C(OCC)C>[ClH:25].[CH2:1]([C:3]1[CH:12]=[C:11]([F:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][NH:16][CH2:17][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69053071HCID 69053071, compound

Product 1

HCID 11673444HCID 11673444, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3aS,9bR)-tert-butyl 8-ethyl-6-fluoro-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the second eluting peak from Example 47, Part D, (60 mg, 0.18 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 to afford 35 mg (71%) of the title compound of Example 48 as a white solid. 1H NMR (DMSO-D6): δ 10.12 (broad s, 1H), 10.00 (broad s, 1H), 8.64 (s, 1H), 7.09 (d, 1H), 6.96 (s, 1H), 3.88-3.82 (m, 1H), 3.61-3.55 (m, 1H), 3.48-3.43 (m, 1H), 3.26-3.20 (m, 1H), 3.18-3.12 (m, 1H), 3.09-3.02 (m, 1H), 2.63 (q, 2H, J=7.7 Hz), 1.18 (t, 3H, J=7.7 Hz). LRMS (ESI): 235.2 (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

Sources & evidence

ORD record
ord-02cfb5fc7fc748a591ca37ceec0c1136
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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