1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58139011, compound

HRID 1622966Notes

Reaction equation

HRID 1622966 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1(O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([C:14]([O:16][CH:19]1[CH2:18][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 228191-IndanolHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanine

Product 1

HCID 58139011HCID 58139011, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(benzyloxy)carbonyl]-2-methylalanine (2.00 g, 8.4 mmol) in DCM (10 ml) at 0° C. was added indanol (2.26 g, 16.9 mmol), EDCI (1.78 g, 9.3 mmol) and finally DMAP (103 mg, 0.8 mmol). The reaction mixture was warmed to RT and stirred for 18 hours. The reaction mixture was washed with 1M HCl (10 ml), sat. Na2CO3 (20 ml), dried (MgSO4) filtered and concentrated in vacuo to leave a brown oil. The crude product was purified by column chromatography (20% EtOAc in heptane) to yield the desired product as a white solid (2.26 g, 76%). LC/MS: m/z 354 [M+H]+.

Workup

  1. washThe reaction mixture was washed with 1M HCl (10 ml), sat. Na2CO3 (20 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto leave a brown oil
  6. customThe crude product was purified by column chromatography (20% EtOAc in heptane)

Sources & evidence

ORD record
ord-00a923d1b32d486fa629a783cc67fec7
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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