Triethylamine → HCID 178455989, compound

HRID 890933Notes

Reaction equation

HRID 890933 reaction equation
[CH2:1]([S:8]([NH:11][C@@H:12]([C:17]([NH:19][C@H:20]([C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([NH2:37])=[NH:36])=[CH:31][CH:30]=1)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[C@@H:13]([CH2:15][CH3:16])[CH3:14])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:45](=O)([O:51]C(C)(C)C)[O:46][C:47]([CH3:50])([CH3:49])[CH3:48].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([S:8]([NH:11][C@@H:12]([C:17]([NH:19][C@H:20]([C:25]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32](/[C:35](/[NH2:37])=[N:36]\[C:45]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:51])=[CH:33][CH:34]=1)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[C@@H:13]([CH2:15][CH3:16])[CH3:14])(=[O:9])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 69623727HCID 69623727, compound

Product 1

HCID 178455989HCID 178455989, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(Benzylsulfonyl)-D-isoleucyl-N1-{4-[amino(imino)-methyl]benzyl}-L-methioninamide (20 mg, 0.032 mmol) was dissolved in dimethylformamide (0.5 ml), to which triethylamine (0.018 ml, 0.13 mmol) and di-t-butyl carbonate (14 mg, 0.065 mnol) were then added and stirred for 16 hours. After addition of ethyl acetate to the reaction mixture, the organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by preparative TLC (dichloromethane:methanol=10:1) to give N-(benzylsulfonyl)-D-isoleucyl-N1-[4-((E)-amino-[[(t-butyloxy)carbonyl]imino]methyl)benzyl]-L-methioninamide (16 mg, 0.024 mmol; yield 76%).

Workup

  1. additionwere then added
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by preparative TLC (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-c90a1655eab84a40b8e5aefb3de7922e
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Reaction notes

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