1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86604861, compound

HRID 1431999Notes

Reaction equation

HRID 1431999 reaction equation
[C:1]1([S:7]([NH:10][C@H:11]([CH2:15][C:16]#[CH:17])[C:12]([OH:14])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:37][O:38][CH:39]([O:42][CH3:43])[CH2:40][NH2:41].CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:37][O:38][CH:39]([O:42][CH3:43])[CH2:40][NH:41][C:12](=[O:14])[C@H:11]([NH:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[CH2:15][C:16]#[CH:17]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 86604862HCID 86604862, compound

Product 1

HCID 86604861HCID 86604861, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-(benzenesulfonamido)pent-4-ynoic acid (11.66 g, 46.04 mmol), HOBt (7.46 g, 55.24 mmol), iPr2NEt (7.13 g, 55.24 mmol), (2,2-dimethoxyethyl)amine (5.81 g, 55.24 mmol), and EDCI (10.53 g, 55.24 mmol) in DMF (100 mL) was stirred for 24 h at RT. The reaction mixture was concentrated and taken up in H2O (100 mL). The aqueous layer was extracted with EtOAc (3×), dried over MgSO4, and concentrated to afford the title compound. 1H NMR (400 MHz, CDCl3): δ 2.43 (m, 2H), 2.71 (s, 3H), 2.85 (s, 1H), 2.89 (s, 3H), 2.96 (m, 2H), 3.98 (t, 7.1 Hz, 3H), 4.15 (t, 5.5 Hz, 1H), 7.55 (m, 3H), 7.80 (d, 8.0 Hz, 2H), 7.97 (s, 1H), 8.11 (t, 5.5 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9981541547294afea16f58ed7c063389
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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