HCID 118276922, compound → HCID 118277087, compound

HRID 1053689Notes

Reaction equation

HRID 1053689 reaction equation
[NH2:1][CH2:2][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)([CH3:9])[CH2:4][C:5](OC)=[O:6].ClCCN(CCCl)C1C=CC(C)=C(C2CNC(=O)C2)C=1>C1(C)C=CC=CC=1>[NH2:16][C:12]1[CH:11]=[C:10]([C:3]2([CH3:9])[CH2:2][NH:1][C:5](=[O:6])[CH2:4]2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 118276922HCID 118276922, compoundHCID 118277068HCID 118277068, compound

Product 1

HCID 118277087HCID 118277087, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a second reaction of the same scale, under comparable conditions, and using comparable procedures, the initially isolated material consisted exclusively of the non-cyclized form (methyl 4-amino-3-(3-aminophenyl)-3-methyl-butanoate) MS (ESI+): m/z=223.20 (M+H)+. The crude material was dissolved/suspended in a sealed tube in toluene (about 25 mL) and heated to about 100° C. (oil bath temperature) for overnight to facilitate lactam formation (TLC reaction control). The organic solution was evaporated under reduced pressure using a rotary evaporator to afford a beige-brown waxy solid that was further purified by silica gel column chromatography using mixtures of dichloromethane (DCM) and methanol (MeOH) as eluent (DCM/MeOH=95:5→93:7) to afford the title compound (4c) as a beige solid. The analytical data corresponded to the proposed structure and was identical to that obtained from the direct lactamization method.

Workup

  1. customIn a second reaction of the same scale
  2. customThe organic solution was evaporated under reduced pressure
  3. customa rotary evaporator
  4. customto afford a beige-brown waxy solid
  5. customthat was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-876496538d8149de842e5da2c5a9ee58
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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