Dichloromethane → HCID 59718448, compound

HRID 656351Notes

Reaction equation

HRID 656351 reaction equation
[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][S:4][S:5]SC(C)(C)C.Cl.C(N=C=N[CH2:37][CH2:38][CH2:39]N(C)C)C.O[N:44]1[C:48](=[O:49])[CH2:47][CH2:46][C:45]1=[O:50].[CH2:51](Cl)Cl>>[O:50]=[C:45]1[CH2:46][CH2:47][C:48](=[O:49])[N:44]1[O:13][C:11](=[O:12])[CH:2]([NH:1][C:14]([O:16][CH2:17][CH:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:3][S:4][S:5][C:38]([CH3:39])([CH3:51])[CH3:37]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131729305HCID 131729305, compound

Product 1

HCID 59718448HCID 59718448, compound

Procedure

To a solution of Fmoc-Cys(SStBu)-OH (1, 2.15 g, 5.0 mmole) dissolved in anhydrous CH2Cl2 (30 mL) was added N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC, 1.146 g, 6 mmole), the reaction mixture was stirred for 10 min. at room temperature (RT) and then added N-hydroxysuccinimide (NHS) (0.690 g, 6.0 mmole). To this reaction mixture was added catalytic amount of N,N′-dimethlyaminopyridine and stirred at RT until completion of reaction tested with TLC. The solvent was evaporated and the residue obtained was extracted with ethyl acetate (50 mL×2), washed with 1M NaHCO3 (10 mL), followed by brine solution (20 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent afforded 2 as a white crystalline solid. Yield. 2.5 g (95%).

Workup

  1. stirringstirred at RT until completion of reaction
  2. customThe solvent was evaporated
  3. customthe residue obtained
  4. extractionwas extracted with ethyl acetate (50 mL×2)
  5. washwashed with 1M NaHCO3 (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5138bdc3206b4759b852bbc05667efc8
Source dataset
uspto-grants-2011_12
Patent number
US08071755B2

Reaction notes

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