1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178453613, compound

HRID 1259439Notes

Reaction equation

HRID 1259439 reaction equation
C(N(C(C)C)CC)(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]([NH2:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:14][CH:15]=1.[CH3:25][C:26]([O:29][C:30]([NH:32][CH2:33][CH:34]1[CH2:39][CH2:38][CH:37]([C:40](O)=[O:41])[CH2:36][CH2:35]1)=[O:31])([CH3:28])[CH3:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:29][C:30](=[O:31])[NH:32][CH2:33][C@H:34]1[CH2:35][CH2:36][C@H:37]([C:40](=[O:41])[NH:24][CH:16]([C:13]2[S:14][CH:15]=[C:11]([Br:10])[CH:12]=2)[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:38][CH2:39]1)([CH3:25])([CH3:28])[CH3:27]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 736918(1r,4r)-4-((((Tert-butoxy)carbonyl)amino)methyl)cyclohexane-1-carboxylic acidHCID 57908828HCID 57908828, compound

Product 1

HCID 178453613HCID 178453613, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C. under N2, diisopropylethylamine (1.1 mL, 6.6 mmol) was added dropwise to a mixture of 1A (564 mg, 2.0 mmol), Boc-tranexamic acid (565 mg, 2.2 mmol), HOBt (297 mg, 2.2 mmol), and EDCI (422 mg, 2.2 mmol) in anhydrous DMF (15 mL). After addition, the mixture was slowly warmed to rt and stirred for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water, 1.0 N HCl, sat. NaHCO3, and brine, dried over MgSO4, filtered, and concentrated. Chromatography on silica gel provided 1B as a light yellow solid. LC/MS m/z 521.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ: 0.8-0-1.0 (m, 2H), 1.45 (s, 9H), 1.25-1.45 (m, 2H), 1.70-1.85 (m, 2H), 1.90-2.05 (2H), 2.95 (2H), 3.05-3.25 (2H), 4.60 (s, broad, 1H), 5.55 (m, 1H), 5.75 (m, 1H), 6.8 (s, 1H), 7.1 (s, 1H), 7.15 (d, J=7.8 Hz, 2H), 7.2-7.35, (m, 3H).

Workup

  1. additionAfter addition
  2. washwashed with water, 1.0 N HCl, sat. NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-408ccae732c64b46b08d74b410adfa1b
Source dataset
uspto-grants-2013_06
Patent number
US08466295B2

Reaction notes

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