1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11699940, compound

HRID 504143Notes

Reaction equation

HRID 504143 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([NH:21][C:22]([C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][N:25]2[S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)(=[O:32])=[O:31])=[O:23])[C:18](O)=[O:19])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>ClCCl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C@H:17]([NH:21][C:22]([C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][N:25]2[S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)(=[O:32])=[O:31])=[O:23])[C:18](=[O:19])[NH:1][CH:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 4192234-AminotetrahydropyranHCID 516892Sodium BicarbonateHCID 66750631HCID 66750631, compound

Product 1

HCID 11699940HCID 11699940, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.094 g (0.94 mmol) of 4-aminotetrahydropyran and 0.48 g (0.94 mmol) of (S)-3-(4-methoxy-phenyl)-2-{[(S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-propionic acid in 50 ml of dichloromethane was added 0.079 g (0.94 mmol) of sodium bicarbonate followed by 0.128 g (0.94 mmol) of HOAT and 0.179 g (0.94 mmol) of EDCI. The mixture was stirred at room temperature for 17 hours after which it was washed with brine and purified by flash chromatography on silica gel, eluting with 50-100% ethyl acetate/heptane to give 0.50 g (0.83 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.00-1.21 (m, 3H); 1.32-1.43 (m, 4H); 1.80 (b, 2H); 2.14 (bd, 1H); 2.69 (t, 1H); 2.99 (dd, 1H); 3.13 (dd, 1H); 3.45 (s, 2H); 3.65 (bd, 1H); 3.78 (s, 3H); 3.87-4.00 (m, 3H); 4.39 (b, 1H); 4.58 (q, 1H); 5.88 (d, 1H); 6.78 (d, 1H); 6.85 (d, 2H); 7.13 (d, 2H); 7.70 (t, 1H); 7.88 (d, 1H); 8.00 (d, 1H); 8.08 (s, 1H).

Workup

  1. washwas washed with brine
  2. custompurified by flash chromatography on silica gel
  3. washeluting with 50-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-092489cc636140dfa3ba489315c250f1
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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