1,2-Dichloroethane → HCID 23589348, compound

HRID 1609822Notes

Reaction equation

HRID 1609822 reaction equation
[OH:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=O.C(Cl)CCl.C1C=CC2N([OH:23])N=NC=2C=1.Cl.[NH2:25][CH:26]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]([NH2:29])=O.[CH3:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C=O)C.CCOC(C)=O>[CH2:32]([O:31][CH2:30][CH:26]([NH:25][C:3]([CH:2]([O:1][C:39]([N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:23])[CH2:6][CH:7]([CH3:9])[CH3:8])=[O:5])[C:27]#[N:29])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 92779(+-)-2-Hydroxyisocaproic acidHCID 22260295HCID 22260295, compound

Product 1

HCID 23589348HCID 23589348, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxyisocaproic acid (0.143 g, 1.0 mmol) was dissolved in 4 mL of DMF and cooled to 0° C. with an ice-water bath. EDC (0.278 g, 1.4 mmol) and HOBT (0.190 g, 1.4 mmol) were added and stirring, under argon, continued for 25 min. To the cold solution was added 2-amino-3-benzyloxy-propionamide hydrochloride (0.250 g, 1.0 mmol), followed by addition of N-methylmorpholine (0.35 mL, 3.2 mmol) and stirring was continued overnight (16 h). The solution was diluted with 100 mL of EtOAc and washed sequentially with a 1.0 M solution of HCl (3×10 mL), a saturated solution of NaHCO3 (3×10 mL), water (100 mL) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated by rotary evaporation to give (0.17 g, 55%) of the crude product which was chromatographed (SiO2, 3% MeOH in EtOAc) to give the desired product (0.11 g, 35%). (d) Morpholine-4-carboxylic acid 1-(2-benzyloxy-1-carbamoyl-ethylcarbamoyl)-3-methyl-butyl Ester

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. custom(16 h)
  4. washwashed sequentially with a 1.0 M solution of HCl (3×10 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customto give (0.17 g, 55%) of the crude product which
  9. customwas chromatographed (SiO2, 3% MeOH in EtOAc)

Sources & evidence

ORD record
ord-eac5730cf098411a8e5b495545370c52
Source dataset
uspto-grants-2006_01
Patent number
US06982263B2

Reaction notes

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