Diisopropylcarbodiimide → HCID 178471824, compound

HRID 1526778Notes

Reaction equation

HRID 1526778 reaction equation
[NH:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=O)[C:2]([NH2:4])=[NH:3].Cl.[CH2:15]([O:17][C:18](=[O:37])[CH2:19][C@H:20]([NH:32][C:33](=[O:36])[CH2:34][NH2:35])[C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[C:23]([Br:31])[CH:22]=1)[CH3:16].O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>CN(C=O)C.ClCCl>[Br:31][C:23]1[CH:22]=[C:21]([C@@H:20]([NH:32][C:33](=[O:36])[CH2:34][NH:35][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[CH:13]=2)[CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:37])[CH:26]=[C:25]([C:27]([CH3:30])([CH3:28])[CH3:29])[CH:24]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86709935(S)-3-(2-Amino-acetylamino)-3-(3-bromo-5-tert-butyl-phenyl)-propionic acid ethyl ester hydrochloride saltHCID 178512495HCID 178512495, compound

Product 1

HCID 178471824HCID 178471824, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-guanidinobenzoic acid (Example C) (179.5 mg, 1.00 mmol), (S)-ethyl 3-(2-aminoacetamido)-3-(3-bromo-5-tert-butyl)phenyl)propanoate hydrochloride (Example H) (439.5 mg, 1.00 mmol) and 1-hydroxybenzotriazole hydrate (31.2 mg, 0.20 mmol) was dissolved in DMF (4 mL) and dichloromethane (4 mL) and stirred at room temperature under nitrogen atmosphere for 10 min to give a colorless suspension. N,N′-diisopropylcarbodiimide (205 uL, 1.33 mmol) was added and the reaction mixture was stirred at room temperature under nitrogen atmosphere overnight. The solvent was evaporated in vacuo to give a yellow viscous residue of the intermediate product: (S)-ethyl 3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido) propanoate. LC-MS analysis of the crude residue shows the desired product's mass: m/z 546 (79BrM+H), m/z 548 (81BrM+H); m/z 568 (79BrM+Na) and m/z 570 (81BrM+Na); Calcd for C25H32BrN5O4: 546.46. The crude residue will be used as such for the saponification (step #2).

Workup

  1. customto give a colorless suspension
  2. customThe solvent was evaporated in vacuo
  3. customto give a yellow viscous residue of the intermediate product

Sources & evidence

ORD record
ord-b752ef02d2264fd2aab2a5ac5ec6ca81
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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