1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68605009, compound

HRID 1593322Notes

Reaction equation

HRID 1593322 reaction equation
Cl.C[NH:3][C@H:4]([C:8]([OH:10])=[O:9])[CH:5]([CH3:7])[CH3:6].[CH:11]1C=CC2N(O)N=NC=2C=1.[F:21][C:22]1[CH:23]=[C:24]([CH2:29][C:30]([OH:32])=O)[CH:25]=[C:26]([F:28])[CH:27]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>ClCCl>[F:28][C:26]1[CH:25]=[C:24]([CH2:29][C:30]([NH:3][C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]([CH3:7])[CH3:6])=[O:32])[CH:23]=[C:22]([F:21])[CH:27]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1454243,5-Difluorophenylacetic acidHCID 16726029N-methyl-valine hydrochloride

Product 1

HCID 68605009HCID 68605009, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl-L-valinate hydrochloride (168 mg) in dichloromethane (6 mL) was added HOBt (135 mg), 3,5-difluorophenylacetic acid (172 mg), EDCI (191 mg) and DIEA (0.522 mL). The reaction mixture was stirred for 16 h, diluted with dichloromethane (50 mL), washed with 5% hydrochloric acid (10 mL) and 10% potassium carbonate (10 mL). The organic layer after drying over anhydrous magnesium sulfate and concentration under reduced pressure afforded the title compound (272 mg). 1H NMR (300 MHz, CDCl3) δ 0.87 (d, 1.5H, J=7 Hz), 0.89 (d, 1.5H, J=7 Hz), 2.01 (m, 1H), 3.58 (s, 2H), 3.63 (s, 3H),4.18 (d,d, 1H, J=6 Hz, J=8 Hz), 7.0 (m, 3H), 8.45 (d, 1H, J=8 Hz). MS APCI, m/z=244(M+1). LC/MS: 1.97 min.

Workup

  1. washwashed with 5% hydrochloric acid (10 mL) and 10% potassium carbonate (10 mL)
  2. dry with materialThe organic layer after drying over anhydrous magnesium sulfate and concentration under reduced pressure

Sources & evidence

ORD record
ord-f2135db7b70e4ba2b7e5ddc95e179db9
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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