1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178474889, compound

HRID 353243Notes

Reaction equation

HRID 353243 reaction equation
[NH:1]([C:8]([CH3:10])=[O:9])[C@H:2]([C:5]([OH:7])=O)[CH2:3][OH:4].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:40]([NH:43][C:44]([C:46]2[NH:47][CH:48]=[C:49]([C:51]3[C:55]([C:56]4[CH:61]=[CH:60][C:59]([CH2:62][NH2:63])=[C:58]([Cl:64])[CH:57]=4)=[CH:54][NH:53][N:52]=3)[CH:50]=2)=[O:45])[CH2:41][OH:42])[CH:36]=[CH:37][C:38]=1[F:39]>CN(C=O)C>[Cl:32][C:33]1[CH:34]=[C:35]([CH:40]([NH:43][C:44]([C:46]2[NH:47][CH:48]=[C:49]([C:51]3[C:55]([C:56]4[CH:61]=[CH:60][C:59]([CH2:62][NH:63][C:5](=[O:7])[CH:2]([NH:1][C:8](=[O:9])[CH3:10])[CH2:3][OH:4])=[C:58]([Cl:64])[CH:57]=4)=[CH:54][NH:53][N:52]=3)[CH:50]=2)=[O:45])[CH2:41][OH:42])[CH:36]=[CH:37][C:38]=1[F:39]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 65249AcetylserineHCID 757711-HydroxybenzotriazoleHCID 178509601HCID 178509601, compound

Product 1

HCID 178474889HCID 178474889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N—Ac-Ser-OH (0.2 mmol) in DMF (5 mL) was added HOBt (0.4 mmol) and EDCI (0.22 mmol) and stirred for 5 min. To the solution was added benzyl amine 11 (0.2 mmol) and TEA (0.3 mmol). The reaction mixture was stirred for 2 h at room temperature. The crude products were purified from preparatory HPLC to afford the desired product II-20 as a white solid. 1HNMR (CD3OD) 8.5 (br, 1H), 7.6 (s, 1H), 7.5 (m, 1H), 7.4 (s, 1H), 7.2-7.3 (m, 3H), 7.1 (t, 1H), 6.8-6.9 (m, 2H), 5.0 (t, 1H), 4.2-4.4 (m, 3H), 3.6-3.7 (m, 4H), 1.9 (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred for 2 h at room temperature
  2. customThe crude products were purified from preparatory HPLC

Sources & evidence

ORD record
ord-8a75e1b809f04922a0d17c2956f38dd2
Source dataset
uspto-grants-2004_06
Patent number
US06750239B2

Reaction notes

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