Triethylamine → HCID 22877428, compound

HRID 1740228Notes

Reaction equation

HRID 1740228 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:44])([CH3:43])[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][NH2:41])=[CH:30][CH:29]=2)[C:17]1=[O:42])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.C(N(CC)CC)C.[CH3:59][O:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=1[N:67]=[C:68]=[O:69]>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:44])([CH3:43])[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][NH:41][C:68]([NH:67][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][C:61]=3[O:60][CH3:59])=[O:69])=[CH:32][CH:33]=2)[C:17]1=[O:42])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 84468TrifluoroacetateHCID 22877437HCID 22877437, compound

Product 1

HCID 22877428HCID 22877428, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg (0.142 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, trifluoroacetate (Example 36, Step A) in 2 mL of dry methylene chloride under nitrogen atmosphere was added 0.040 mL (0.28 mmol) of triethylamine followed by 0.021 mL (0.16 mmol) of 2-methoxyphenyl isocyanate. The reaction mixture was stirred at room temperature for 30 minutes, diluted with 100 mL of ethyl acetate, washed with 25 mL of saturated aqueous ammonium chloride, 25 mL of saturated aqueous sodium bicarbonate and 25 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvent removed under vacuum to afford 102 mg (97%) of the product as a white foam. 1H NMR (200 MHz, CD3OD): δ 1.38 (s, 6H), 1.80 (m, 1H), 2.15-2.50 (m, 3H), 3.80 (s, 3H), 4.19 (s, 2H), 4.27 (m, 1H), 4.68 (d, 16 Hz, 1H), 5.00 (s, 2H), 5.30 (d, 16 Hz, 1H), 6.90 (m, 3H), 7.10-7.45 (m, 17H), 7.92 (m, 1H). FAB-MS: calculated for C44H45N5O6 739; found 740 (M+H, 60%).

Workup

  1. washwashed with 25 mL of saturated aqueous ammonium chloride, 25 mL of saturated aqueous sodium bicarbonate and 25 mL of brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-43fbddbea9b44d4fb9abd541c7959c50
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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