4-Methylmorpholine → 2-[(2E,4E,6E,8E]-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino)-5-hydroxyphenyl butanoate

HRID 1375284Notes

Reaction equation

HRID 1375284 reaction equation
[CH3:1]/[C:2](/[CH:15]=[CH:16]/[CH:17]=[C:18](\[CH3:30])/[CH:19]=[CH:20]/[C:21]1[C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][CH2:23][C:22]=1[CH3:29])=[CH:3]\[C:4]([N-:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[OH:14])=[O:5].CN1CCOCC1.[C:38](Cl)(=[O:42])[CH2:39][CH2:40][CH3:41].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[C:38]([O:14][C:8]1[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=1[NH:6][C:4](=[O:5])/[CH:3]=[C:2](\[CH3:1])/[CH:15]=[CH:16]/[CH:17]=[C:18](\[CH3:30])/[CH:19]=[CH:20]/[C:21]1[C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][CH2:23][C:22]=1[CH3:29])(=[O:42])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8855Butyryl chlorideHCID 11430Potassium CarbonateHCID 178424935HCID 178424935, compound

Product 1

HCID 103449782-[(2E,4E,6E,8E]-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino)-5-hydroxyphenyl butanoateYield 84.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoyl]-(2,4-dihydroxy)phenylamide (KCBG08) (0.10 g, 0.24 mmol) was dissolved in anhydrous CH2Cl2 (15 mL), and NMM (0.049 g, 0.49 mmol) was added. To the resulting mixture was added dropwise butyryl chloride (0.050 mL, 0.49 mmol) at 0° C., and the resulting solution was stirred for 0.5 h. Finely ground K2CO3 (0.30 g) and MeOH (3 mL) was added to the reaction mixture. After stirring for 1 h, the completion of the reaction was confirmed by TLC. The mixture was washed with CH2Cl2 (30 mL) and H2O (20 mL). The organic layer was dried over anhydrous MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography over silica gel (EtOAc:hexane=1:4) to give 2-[(2E,4E,6E,8E]-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino)-5-hydroxyphenyl butanoate (KCBG10, 97 mg, 83%) as a yellow solid.

Workup

  1. stirringAfter stirring for 1 h
  2. washThe mixture was washed with CH2Cl2 (30 mL) and H2O (20 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography over silica gel (EtOAc:hexane=1:4)

Sources & evidence

ORD record
ord-941415ad44c34aca96716cd37e595e6f
Source dataset
uspto-grants-2007_01
Patent number
US07166744B2

Reaction notes

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