Dichloromethane → Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

HRID 1796879Notes

Reaction equation

HRID 1796879 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]([OH:13])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.Cl.C(N=C=N[CH2:26][CH2:27][CH2:28]N(C)C)C.[CH3:32][C:33]1[CH2:38][CH2:37][CH2:36][C:35]([CH3:40])([CH3:39])[C:34]=1/[CH:41]=[CH:42]/[C:43](/[CH3:52])=[CH:44]/[CH:45]=[CH:46]/[C:47](/[CH3:51])=[CH:48]/[CH2:49]O>CN(C)C=O>[CH3:51]/[C:47](/[CH:46]=[CH:45]/[CH:44]=[C:27](\[CH3:26])/[CH:28]=[CH:41]/[C:34]1[C:35]([CH3:39])([CH3:40])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[CH:48]\[CH2:49][O:15][C:14](=[O:16])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][C:11]([O:13][CH2:49]/[CH:48]=[C:47](\[CH3:51])/[CH:46]=[CH:45]/[CH:44]=[C:43](\[CH3:52])/[CH:42]=[CH:41]/[C:34]1[C:35]([CH3:40])([CH3:39])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[O:12]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 99718N-(tert-butoxycarbonyl)-L-aspartic acidHCID 445354RetinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86590977Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc aspartic acid (1.2 mg), methylene chloride 20 ml and minimum amount of dimethylformamide (DMF) were added to nitrogen filled, three mouth- round bottom flask and melted. The reaction mixture was cooled down into 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [EDCI](1.36 g)were added slowly, and stirred for approximately 30 minutes. Retinol (0.51 g) was added into the reaction mixture, small amount of N,N′-dimethylaminopyridine (DMAP) were added immediately, and stirred for approximately 1˜3 hours. After the reaction was finished, eluent were removed under the low pressure, the residues were melted with ethyl acetate and washed several times with water and Brine. Organic phase were dried with anhydrous MgSO4, concentrated under low pressure and separated with column chromatography.

Workup

  1. additionfilled
  2. additionwere added immediately
  3. stirringstirred for approximately 1˜3 hours
  4. customeluent were removed under the low pressure
  5. washwashed several times with water and Brine
  6. dry with materialOrganic phase were dried with anhydrous MgSO4
  7. concentrationconcentrated under low pressure
  8. customseparated with column chromatography

Sources & evidence

ORD record
ord-cf1da0af55b84698803c304c84df7561
Source dataset
uspto-grants-2006_04
Patent number
US07030265B2

Reaction notes

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