4-Methylmorpholine → HCID 86592732, compound

HRID 2251909Notes

Reaction equation

HRID 2251909 reaction equation
CN1CCOCC1.[CH3:8][N:9]([CH3:27])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[CH2:26][CH2:25][CH2:24][C@@H:20]2[C:21]([OH:23])=O)=[O:18])=[CH:12][CH:11]=1.ClC(OCC)=O.Cl.[Br:35][C:36]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:37]=1[CH2:38][O:39][C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH2:42]>O.C1(C)C=CC=CC=1>[Br:35][C:36]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:37]=1[CH2:38][O:39][C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH:42][C:21]([C@H:20]1[CH2:24][CH2:25][CH2:26][N:19]1[C:17](=[O:18])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([N:9]([CH3:8])[CH3:27])=[CH:15][CH:14]=1)=[O:23]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 229341702-[(2-Bromo-4-chlorophenyl)methoxy]aniline--hydrogen chloride (1/1)HCID 57426175HCID 57426175, compound

Product 1

HCID 86592732HCID 86592732, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Toluene (111 ml) and N-methylmorpholine (3.85 ml, 35.0 mmol) were added to N-[(4-dimethylaminophenyl)acetyl]-D-proline (8.56 g, 31.0 mmol). Ethyl chloroformate (3.26 ml, 34.1 mmol) was added to the obtained mixture, and they were stirred for 2 hours. 2-(2-Bromo-4-chlorobenzyloxy)aniline hydrochloride (10.8 g, 31.0 mmol) and N-methylmorpholine (4.09 ml, 37.2 mmol) were added thereto and they were stirred at room temperature overnight. Water (40 ml) was added to the reaction mixture. The organic layer was washed with water (40 ml) and then dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with methylene chloride and methanol (30:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain the title compound in the form of a yellow solid (16.3 g, 92%).

Workup

  1. stirringthey were stirred at room temperature overnight
  2. washThe organic layer was washed with water (40 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washAfter the elution with methylene chloride and methanol (30:1), suitable fractions
  6. customwere collected
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-20eeae9889964b38a20173f832a627fd
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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