Triethylamine → HCID 178439611, compound

HRID 1781207Notes

Reaction equation

HRID 1781207 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.FC1C(O)=C(F)C(F)=C(F)C=1F.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.Cl.[NH2:62][CH2:63][CH2:64][C:65]1[N:69]=[CH:68][NH:67][CH:66]=1>C(OCC)(=O)C.CN(C)C=O>[NH:67]1[CH:66]=[C:65]([CH2:64][CH2:63][NH:62][C:26](=[O:27])[C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]2[CH:1]3[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]2[CH2:4]4)[CH2:8]3)([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:29])[N:69]=[CH:68]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophanHCID 178478691HCID 178478691, compound

Product 1

HCID 178439611HCID 178439611, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added pentafluorophenol (0.189 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (0.200 g, 1.04 mmol). This mixture was stirred 2 hours, then triethylamine (0.36 mL, 2.6 mmol) and histamine dihydrochloride (0.240 g, 1.30 mmol) were added. After stirring an additional 40 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with water. The organic phase was dried over MBSO4, concentrated, purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant), and dried for 48 hours under vacuum at 70° C. to provide 0.234 g (47%) of product; 1H NMR (CDCl3) δ1.40-1.60 (2H, m), 1.57 (3H, s), 1.65-2.00 (13H, m), 2.65-2.75 (2H, m), 3.25-3.45 (4H, m), 4.82 (1H, br s), 5.42 (1H, br s), 6.67 (1H, s), 6.81 (1H, br s), 6.91 (1H, br s),7.00-7.20 (2H, m), 7.34 (1H, d, J 7 Hz), 7.46 (1H, s), 7.55 (1H, d, J 7 Hz), 8.67 (1H, br s).

Workup

  1. stirringAfter stirring an additional 40 hours
  2. washwashed with water
  3. customThe organic phase was dried over MBSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant)
  6. customdried for 48 hours under vacuum at 70° C.

Sources & evidence

ORD record
ord-7194255956584fd99d5e7200184f0486
Source dataset
uspto-grants-1997_05
Patent number
US05631281

Reaction notes

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