1,2-Dichloroethane → N-(tert-Butoxycarbonyl)-4-(iso-propylcarbamoyl-methyl)-benzylamine

HRID 1191042Notes

Reaction equation

HRID 1191042 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20]([NH2:23])([CH3:22])[CH3:21].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17](=[O:19])[NH:23][CH:20]([CH3:22])[CH3:21])=[CH:14][CH:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6363IsopropylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27559832-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acid

Product 1

HCID 58495494N-(tert-Butoxycarbonyl)-4-(iso-propylcarbamoyl-methyl)-benzylamineYield 92.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine [4-(tert-butoxycarbonylaminomethyl)-phenyl]-acetic acid (400 mg, 1.5 mmol), isopropylamine (0.14 mL, 1.65 mmol), EDC (345 mg, 1.8 mmol), HOBt (243 mg, 1.8 mmol), triethylamine (0.63 mL, 4.5 mmol) and DMAP (18.3 mg, 0.15 mmol) in anhydrous DCM (15 mL). Stir at room temperature for 1 day under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1) to obtain the desired intermediate as a white solid (426 mg, 92%). MS (ES+) m/z: 324 (M+NH4+)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-dceda05de27a48999e704d316175c3fe
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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