1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67316034, compound

HRID 2059899Notes

Reaction equation

HRID 2059899 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:31]([O:35][C:36](=[O:56])[CH2:37][C@H:38]([NH:42][S:43]([C:46]1[C:51]([CH3:52])=[CH:50][C:49]([O:53][CH3:54])=[CH:48][C:47]=1[CH3:55])(=[O:45])=[O:44])[C:39](O)=[O:40])([CH3:34])([CH3:33])[CH3:32].[CH3:57][O:58][CH:59]([O:62][CH3:63])[CH2:60][NH2:61]>C(Cl)Cl>[CH3:57][O:58][CH:59]([O:62][CH3:63])[CH2:60][NH:61][C:39](=[O:40])[C@@H:38]([NH:42][S:43]([C:46]1[C:51]([CH3:52])=[CH:50][C:49]([O:53][CH3:54])=[CH:48][C:47]=1[CH3:55])(=[O:44])=[O:45])[CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:56]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 67315296HCID 67315296, compound

Product 1

HCID 67316034HCID 67316034, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Diisopropylethylamine (2.5 eq) followed by HOBT (1.0 eq) and EDCI (1.5 eq) was added to a solution of (S)-4-tert-butoxy-2-(4-methoxy-2,6-dimethylphenyl-sulfonamido)-4-oxobutyric acid (1.91 mmol, 1.0 eq) in DCM (10 ml/mmol) at 0° C. The resulting solution was stirred for 15 min at 25° C., cooled to 0° C. again and 2,2-dimethoxyethanamine (1.2 eq) was added. The reaction mixture was stirred for 16 h at 15° C. It was then diluted with DCM and extracted with saturated ammonium chloride solution, saturated sodium chloride solution, saturated sodium bicarbonate solution and finally saturated sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated to low volume under vacuum. The crude product was processed by column chromatography. Yield: 70%

Workup

  1. temperaturecooled to 0° C. again
  2. stirringThe reaction mixture was stirred for 16 h at 15° C
  3. extractionextracted with saturated ammonium chloride solution, saturated sodium chloride solution, saturated sodium bicarbonate solution and finally saturated sodium chloride solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated to low volume under vacuum

Sources & evidence

ORD record
ord-9f40db861f534316972c071f18fcc4ad
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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