4-Methylmorpholine → HCID 54271608, compound

HRID 1584407Notes

Reaction equation

HRID 1584407 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:32]([O:36][NH2:37])([CH3:35])([CH3:34])[CH3:33].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:20][CH:19]=1)[C:13]([NH:37][O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 53980138HCID 53980138, compound

Product 1

HCID 54271608HCID 54271608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above-prepared (R)-2-(benzyloxycarbonylamino)-3-(4-phenoxyphenylthio)-propionic acid was dissolved in methylene chloride (175 ml), cooled to 0° C., and treated with O-(tert-butyl)hydroxylamine hydrochloride (7.7 g), 4-methylmorpholine (9.4 ml), 1-hydroxybenzotriazole (2.8 g), and N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide (7.9 g). The mixture was allowed to warm to room temperature, stirred for 1.5 hours, then partitioned between methylene chloride and water. Solvent was removed from the organic phase under reduced pressure, and the residue purified by flash chromatography on silica gel, eluting with 0 to 50% ethyl acetate/hexane, to provide (R)-2 -(benzyloxycarbonylamino)-N-tert-butoxy-3-(4-phenoxyphenylthio)-propionamide (7.4 g) as a white foam.

Workup

  1. temperatureto warm to room temperature
  2. custompartitioned between methylene chloride and water
  3. customSolvent was removed from the organic phase under reduced pressure
  4. customthe residue purified by flash chromatography on silica gel
  5. washeluting with 0 to 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-27fe589ec1274fa8b708902e82b567ed
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

Loading…