Dicyclohexylcarbodiimide → 2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide

HRID 455542Notes

Reaction equation

HRID 455542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([NH:25][C@H:26]([C:31](O)=[O:32])[C@H:27]([CH2:29][CH3:30])[CH3:28])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[C:18]([NH:25][CH:26]([CH:27]([CH3:28])[CH2:29][CH3:30])[C:31]([NH:17][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:32])([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]

Participants

5

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 134772DidesmethylsibutramineHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 673857212-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

250 mg of 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (II) and 210 mg of Boc-isoleucine (R in Formula is Boc) was dissolved in anhydrous THF (5 mL). 220 mg DCC was dissolved in 25 mL anhydrous THF. The solution of DCC in THF was added dropwisely into the reaction solution, and then stirred overnight at room temperature to give white precipitate. The solid was filtered off and washed for at least three times with anhydrous ethyl ether. The filtrate and washed ethyl ether were collected, evaporated and purified by column chromatography to give title compound 2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide (Formula I, wherein R is Boc).

Workup

  1. customto give white precipitate
  2. filtrationThe solid was filtered off
  3. washwashed for at least three times with anhydrous ethyl ether
  4. washThe filtrate and washed ethyl ether
  5. customwere collected
  6. customevaporated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-d065b5ae9cbd43f6adfce258ba1c4684
Source dataset
uspto-grants-2013_07
Patent number
US08497305B2

Reaction notes

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