1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(4-methylbenzenesulfonamido)pent-4-ynamide

HRID 2219881Notes

Reaction equation

HRID 2219881 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13](O)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C=[N:23]C2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-].CCN=C=NCCCN(C)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13]([NH2:23])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10978432(R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid

Product 1

HCID 86604882(R)-2-(4-methylbenzenesulfonamido)pent-4-ynamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-(4-methylphenyl sulfonamido)pent-4-ynoic acid (1.0 g, 3.7 mmol), HOAt (0.76 g, 5.6 mmol), iPr2NEt (2.17 g, 16.9 mmol), NH4Cl (0.6 g, 11 mmol), and EDCI (1.07 g, 5.61 mmol) in 20 mL DMF was stirred for 18 h at RT. Water was added, which caused a precipitate to form. The white solid was filtered and air dried to afford the title compound. MS (m/z, m+1): 267.3.

Workup

  1. customto form
  2. filtrationThe white solid was filtered
  3. customair dried

Sources & evidence

ORD record
ord-1dd3279a79fe422c93fd7891c6e3bdaf
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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