1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 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 1375283Notes

Reaction equation

HRID 1375283 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][C:13]1[CH2:18][CH2:17][CH2:16][C:15]([CH3:20])([CH3:19])[C:14]=1/[CH:21]=[CH:22]/[C:23](/[CH3:33])=[CH:24]/[CH:25]=[CH:26]/[C:27](/[CH3:32])=[CH:28]/[C:29]([OH:31])=O.[C:34]([O:39][C:40]1[CH:45]=[C:44]([OH:46])[CH:43]=[CH:42][C:41]=1[NH2:47])(=[O:38])[CH2:35][CH2:36][CH3:37]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:34]([O:39][C:40]1[CH:45]=[C:44]([OH:46])[CH:43]=[CH:42][C:41]=1[NH:47][C:29](=[O:31])/[CH:28]=[C:27](\[CH3:32])/[CH:26]=[CH:25]/[CH:24]=[C:23](\[CH3:33])/[CH:22]=[CH:21]/[C:14]1[C:15]([CH3:19])([CH3:20])[CH2:16][CH2:17][CH2:18][C:13]=1[CH3:12])(=[O:38])[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 444795Retinoic AcidHCID 690238032-Amino-5-hydroxy-phenyl butanoate

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 79.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent3×

Procedure

To a solution of EDCI (0.023 g, 0.12 mmol) in anhydrous DMF (5 mL) was added a solution of retinoic acid (0.031 g, 0.10 mmol) in anhydrous DMF (5 mL). The mixture was stirred at room temperature for 0.5 h. A solution of 2-amino-5-hydroxy-phenyl butanoate (KCBG05, 0.020 g, 0.12 mmol) and DMAP (cat.) in anhydrous DMF (2 mL) was added to the mixture, and again stirred for 4 h. The reaction was quenched with NH4Cl (aq.), extracted with EtOAc (2×30 mL). The extracts were washed with H2O (2×30 mL), dried over anhydrous Na2SO4, and evaporated. The residue was purified by flash column chromatography over silica gel (EtOAc:hexane=1:6) 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, 0.038 g, 78%) as a yellow solid.

Workup

  1. stirringagain stirred for 4 h
  2. customThe reaction was quenched with NH4Cl (aq.)
  3. extractionextracted with EtOAc (2×30 mL)
  4. washThe extracts were washed with H2O (2×30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash column chromatography over silica gel (EtOAc:hexane=1:6)

Sources & evidence

ORD record
ord-5270ea83cae04571bd8cd9ec72dbb1ab
Source dataset
uspto-grants-2007_01
Patent number
US07166744B2

Reaction notes

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