1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 503192, compound

HRID 2393520Notes

Reaction equation

HRID 2393520 reaction equation
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:20][C@@H:21]([OH:41])[C@@H:22]([NH:30]C(OCC1C=CC=CC=1)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li].[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH2:49][O:50][C:51]([NH:53][C@H:54]([C:59]([OH:61])=O)[C@H:55]([CH2:57][CH3:58])[CH3:56])=[O:52].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C=O)C.CCOCC.[Pd].CO>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:10][N:9]1[CH2:20][C@@H:21]([OH:41])[C@@H:22]([NH2:30])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:10][N:9]1[CH2:20][C@@H:21]([OH:41])[C@@H:22]([NH:30][C:59](=[O:61])[C@H:54]([C@H:55]([CH2:57][CH3:58])[CH3:56])[NH:53][C:51]([O:50][CH2:49][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][N:43]=1)=[O:52])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

11

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 503167HCID 503167, compoundHCID 3028194LithiumHCID 54304856HCID 54304856, compound

Product 2

HCID 503192HCID 503192, compoundYield 161.8%HCID 22870891HCID 22870891, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

N-tert-butyl-1-{3(S)-amino-2(R)-hydroxy-4-phenylbutyl}-4(R)-phenylpiperidine-2(S)-carboxamide {prepared by hydrogenolysis (5% Pd/C, 1 atmosphere, MeOH, 2h) from 0.605 mg (0.108 mmol) of N-tert-butyl-1-{3(S)-(benzyloxycarbonylamino)-2(R)-hydroxy-4-phenylbutyl}-4(R)-phenylpiperidine-2(S)-carboxamide (see entry 1 of Table I)} was dissolved in DMF (1.6 mL). The lithium salt of N-{(2-pyridinylmethoxy)carbonyl}isoleucine (586 mg, 0.228 mmol), 1-hydroxybenzotriazole (32 mg, 0.237 mmol) and N-ethyl-N'-{3-(dimethylamino)propyl}carbodiimide (45.4 mg, 0.237 mmol) were added to the solution. The mixture was stirred at room temperature for 18 h. Thereafter, the reaction mixture was diluted with Et2O, washed with H2O , a saturated aqueous solution of NaHCO3 (2×) and brine, dried (MgSO4) and evaporated to dryness. The resulting yellow oil was purified by flash chromatography (SiO2, eluent: CHCl3, MeOH, 97.5:2.5 and then 95:5) to give the title compound as a white solid (58.7 mg). FAB mass spectrum, m/z: 672 (M+H)+.

Workup

  1. washwashed with H2O
  2. dry with materiala saturated aqueous solution of NaHCO3 (2×) and brine, dried (MgSO4)
  3. customevaporated to dryness
  4. customThe resulting yellow oil was purified by flash chromatography (SiO2, eluent

Sources & evidence

ORD record
ord-72407488692b4dcf8e281b4ca29f15c9
Source dataset
uspto-grants-1998_09
Patent number
US05807870

Reaction notes

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