1,2-Dichloroethane → HCID 18474610, compound

HRID 2228005Notes

Reaction equation

HRID 2228005 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][S:18][CH3:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH:27](O)[CH3:28])[CH2:22][CH2:21]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][S:18][CH3:19])[C:13]([O:15][CH:27]([CH2:26][N:23]1[CH2:24][CH2:25][O:20][CH2:21][CH2:22]1)[CH3:28])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 97806N-benzyloxycarbonyl-DL-methionineHCID 979574-Morpholineethanol, .alpha.-methyl-

Product 1

HCID 18474610HCID 18474610, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(benzyloxycarbonylamino)-4-methylsulfanylbutyric acid (1.13 g; 2.76 mmol), 1-(morpholino)propan-2-ol (0.57 ml; 4 mmol), EDC (0.768 g; 4 mmol), DMAP (0.488 g; 4 mmol) in dichloromethane (5 ml) was stirred overnight at ambient temperature. After evaporation of the solvent, the residue was purified by flash chromatography eluting with dichloromethane/ethanol (97/3) to give 1-(morpholinoprop-2-yl 2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate as a foam. Yield=55%.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by flash chromatography
  3. washeluting with dichloromethane/ethanol (97/3)

Sources & evidence

ORD record
ord-e0bcc7dfcf804909a916361109d7a52d
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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