Hydrochloric Acid → HCID 57267684, compound

HRID 249570Notes

Reaction equation

HRID 249570 reaction equation
[CH2:1]([S:8][CH2:9][C@H:10]([C:26](O)=[O:27])[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:30]([O:32][C:33](=[O:36])[CH2:34][NH2:35])[CH3:31].ON1C2C=CC=CC=2N=N1.Cl>CN(C)C=O.CN1CCOCC1>[CH2:30]([O:32][C:33](=[O:36])[CH2:34][NH:35][C:26](=[O:27])[C@@H:10]([CH2:9][S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[NH:11][C:12](=[O:25])[C:13]([CH3:23])([CH3:24])[CH2:14][S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 2723640Glycine ethyl ester, hydrochlorideHCID 14969991HCID 14969991, compound

Product 1

HCID 57267684HCID 57267684, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 79724-MethylmorpholineSolvent

Procedure

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethyl-propionyl)-D-cysteine (0.32 g) and glycine ethyl ester hydro-chloride (0.12 g) in N,N-dimethylformamide (DMF, 3 ml), N-methylmorpholine (NMM, 0.19 ml), 1-hydroxybenzotriazole (HOBt, 0.17 g) and then a solution of N,N,-dicyclohexylcarbodiimide (DCC, 0.18 g) in DMF (2 ml) were added under ice cooling. The mixture was stirred for 2 hr. at 0° C. and for 2 hr. at room temperature, and stood overnight. 1 N hydrochloric acid (30 ml) was added into the reaction mixture and the mixture was extracted with ether. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.35 g (91%) of the titled compound.

Workup

  1. waitat 0° C. and for 2 hr
  2. waitat room temperature, and stood overnight
  3. extractionthe mixture was extracted with ether
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-fe97a119812640138cecd7bc6614fac0
Source dataset
uspto-grants-1993_05
Patent number
US05214181

Reaction notes

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