1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67423004, compound

HRID 571439Notes

Reaction equation

HRID 571439 reaction equation
[C:1]([NH:8][C@H:9]([C:30](O)=[O:31])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Sn:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:34][O:35][C:36](=[O:46])[C@H:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH2:38].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:34][O:35][C:36](=[O:46])[C@H:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH:38][C:30](=[O:31])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 67423690HCID 67423690, compound

Product 1

HCID 67423004HCID 67423004, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To N-Boc-4-(tributylstannyl)-L-phenylalanine (1.67 g, 3.00 mmol, 1.00 equiv) and L-phenylalanine methyl ester hydrochloride (647 mg, 3.00 mmol, 1.00 equiv) in CH2Cl2 (30 mL) at 0° C. was added EDCI (1.15 g, 6.00 mmol, 2.00 equiv), HOBt (810 mg, 6.00 mmol, 2.00 equiv), n,n-diisopropylethyl amine (1.56 mL, 9.00 mmol, 3.00 equiv) and 4-(Dimethylamino)pyridine (36 mg, 0.30 mmol, 0.10 equiv). After stirring for 1 hr at 0° C., the reaction mixture was allowed to stirred at room temperature for 12 hr. The reaction mixture was quenched with water (20 mL), and CH2Cl2 (10 mL) was added. The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organic phases were washed with brine (10 mL) and dried (Na2SO4). concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with hexane/EtOAc 3:1 (v/v) to afford 1.72 g of the title compound as a white foam (80% yield).

Workup

  1. stirringto stirred at room temperature for 12 hr
  2. customThe reaction mixture was quenched with water (20 mL), and CH2Cl2 (10 mL)
  3. additionwas added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  6. washThe combined organic phases were washed with brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel eluting with hexane/EtOAc 3:1 (v/v)

Sources & evidence

ORD record
ord-1fa9ff9ccec94647b4828620e9df71de
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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