Triethylamine → HCID 22877435, compound

HRID 1740227Notes

Reaction equation

HRID 1740227 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][C:13]([CH3:45])([CH3:44])[C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH2:41][NH2:42])=[CH:31][CH:30]=2)[C:18]1=[O:43])=[O:15])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:53][N:54]=[C:55]=[O:56]>C(Cl)Cl>[CH2:2]([O:9][C:10]([NH:12][C:13]([CH3:45])([CH3:44])[C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH2:41][NH:42][C:55]([NH:54][CH3:53])=[O:56])=[CH:33][CH:34]=2)[C:18]1=[O:43])=[O:15])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 131720218HCID 131720218, compound

Product 1

HCID 22877435HCID 22877435, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.57 g (13.7 mmol) of 2-benzyloxycarbonylamino-2-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(aminomethyl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzazepin-3(R)-yl]-propanamide, hydrochloride (Step I) in 75 mL of dry methylene chloride under nitrogen atmosphere was added 2.28 mL (16.4 mmol) of triethylamine followed by 0.89 mL (15 mmol) of methyl isocyanate. After stirring at room temperature for 45 minutes the solvent was removed under vacuum. The resulting material was dissolved in methylene chloride and purified by flash column chromatography on silica gel eluting with ethyl acetate/methanol (96:4) to afford 7.73 g (87%) of product as a white foam. 1H NMR (200 MHz, CD3OD): δ 1.39 (s, 6H), 1.82 (m, 1H), 2.15-2.60 (m, 3H), 2.63 (s, 3H), 4.13 (s, 2H), 4.36 (m, 1H), 4.86 (d, 15 Hz, 1H), 4.85 (s, 2H), 5.32 (d, 15 Hz, 1H), 7.08-7.43 (m, 17H). FAB-MS: calculated for C38H41N5O5 647; found 648(M+H, 80%).

Workup

  1. customwas removed under vacuum
  2. dissolutionThe resulting material was dissolved in methylene chloride
  3. custompurified by flash column chromatography on silica gel eluting with ethyl acetate/methanol (96:4)

Sources & evidence

ORD record
ord-aed486ef69a144d6bd1975db9ccdd1a7
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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