Acetic Anhydride → (S)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl]propyl acetate

HRID 222544Notes

Reaction equation

HRID 222544 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:41](OC(=O)C)(=[O:43])[CH3:42]>ClCCl>[C:41]([O:33][C@H:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([OH:32])([CH3:31])[CH3:30])(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54563620C29H28ClNO2

Product 1

HCID 58260879(S)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl]propyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-[2-[3(S)-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxy propyl]phenyl]-2-propanol (100 gm) in dichloromethane (500 ml) at 25-30° C. 4-di(methyl amino)pyridine (5.32 gm) was added and cooled to 0° C. To the reaction mixture Triethylamine (26.4 gm) was added at 0° C. Acetic anhydride (26.7 gm) was added slowly at temp. 0-5° C. over 30-60 min and maintained the reaction at temp. 0-5° C. over 30 min. Reaction completion was monitored by TLC. After reaction completion the reaction mass was quenched into 7% NaHCO3(500 ml) and stirred for 15 min. Temperature was raised to 25-30° C. and maintained for 30 min. Reaction mass was settled for 15 min and separated the organic layer. Aq.layer was extracted with dichloromethane (250 ml). The combined organic layer was washed with 25% NH4Cl solution (500 ml). Organic layer was distilled below 40° C. to get the desired product as residue.

Workup

  1. customat 25-30° C
  2. temperaturemaintained
  3. customthe reaction at temp
  4. wait0-5° C. over 30 min
  5. customReaction completion
  6. customAfter reaction completion the reaction mass
  7. customwas quenched into 7% NaHCO3(500 ml)
  8. temperatureTemperature was raised to 25-30° C.
  9. temperaturemaintained for 30 min
  10. customReaction mass
  11. waitwas settled for 15 min
  12. customseparated the organic layer
  13. extractionAq.layer was extracted with dichloromethane (250 ml)
  14. washThe combined organic layer was washed with 25% NH4Cl solution (500 ml)
  15. distillationOrganic layer was distilled below 40° C.

Sources & evidence

ORD record
ord-eced30d741be426092c8d4989e3ff25b
Source dataset
uspto-grants-2012_06
Patent number
US08207343B2

Reaction notes

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