Hydrochloric Acid → HCID 131720218, compound

HRID 1379852Notes

Reaction equation

HRID 1379852 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:51])([CH3:50])[C:13]([NH:15][C@@H:16]1[CH2:22][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH2:40][NH:41]C(OC(C)(C)C)=O)=[CH:30][CH:29]=2)[C:17]1=[O:49])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:52]>CO>[ClH:52].[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:51])([CH3:50])[C:13]([NH:15][C@@H:16]1[CH2:22][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH2:40][NH2:41])=[CH:32][CH:33]=2)[C:17]1=[O:49])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22877438HCID 22877438, compound

Product 1

HCID 131720218HCID 131720218, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 9.83 g (0.55 mmol) of 2-benzyloxycarbonylamino-2-methyl- N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-[(t-butoxycarbonylamino)methyl][1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-3(R)-yl]propanamide (Step H) in 170 mL of methanol was added 120 mL of 9 N aqueous hydrochloric acid. Periodically 10 mL portions of methanol were added to the reaction mixture to dissolve precipitates which form during the reaction (50 mL total). The reaction mixture was stirred overnight at room temperature then the solvent was removed under vacuum. The resulting oil was dissolved in methanol and the solvent was removed under vacuum to afford 8.57 g (96%) of the title compound as an off-white foam. 1H NMR (200 MHz, CD3OD): δ 1.40 (s, 6H), 1.90 (m, 1H), 2.20-2.65 (m, 3H), 4.02 (s, 2H), 4.32 (m, 1H), 4.96 (d, 16 Hz, 1H), 5.00 (s, 2H), 5.25(d, 16 Hz, 1H), 7.08-7.65 (m, 17H). FAB-MS: calculated for C36H38N4 O4 590; found 591(M+H, 100%).

Workup

  1. dissolutionto dissolve
  2. customprecipitates which
  3. customform during the reaction (50 mL total)
  4. customthe solvent was removed under vacuum
  5. dissolutionThe resulting oil was dissolved in methanol
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8db95db80d804e7d80cc251b5fb2d7d9
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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