1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59607757, compound

HRID 70918Notes

Reaction equation

HRID 70918 reaction equation
OC(C(F)(F)F)=O.[C:8]([O:12][C:13]([N:15]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:16]([CH3:20])[C:17]([OH:19])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:48]([O:50][C:51](=[O:69])[CH2:52][C@H:53]([NH2:68])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([Cl:67])[CH:62]=2)=[CH:57][CH:56]=1)[CH3:49]>C1COCC1.C(#N)C.O>[CH2:48]([O:50][C:51](=[O:69])[CH2:52][C@H:53]([NH:68][C:17](=[O:19])[CH:16]([N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:20])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([Cl:67])[CH:62]=2)=[CH:57][CH:56]=1)[CH3:49]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59607537HCID 59607537, compoundHCID 131730297HCID 131730297, compound

Product 1

HCID 59607757HCID 59607757, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a suspension of 2-(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-propionic acid TFA salt (197 mg, 0.714 mmol) in THF (10 ml) at room temperature is added EDCI (219 mg, 1.142 mmol) and HOBT (164 mg, 1.071 mmol). The mixture is stirred at room temperature for 10 mins and then was added a solution of (R)-3-amino-4-(3′-chloro-biphenyl-4-yl)-butyric acid ethyl ester (202 mg, 0.571 mmol) in THF and TEA (0.199 ml, 1.428 mmol). The mixture is stirred at room temperature. Reverse phase HPLC [30 to 90% ACN—H2O (0.1% TFA) over 10 min by X-Bridge phenyl column] give the title compound (290 mg, 71% yield). LCMS (condition B): 575 (M+1); retention time=1.52 min.

Workup

  1. stirringThe mixture is stirred at room temperature

Sources & evidence

ORD record
ord-d311dc67f9ed49b698a218330e558b4c
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

Loading…