Benzoyl Peroxide → 6-Aminohexanoic Acid

HRID 466245Notes

Reaction equation

HRID 466245 reaction equation
BrN1C(=[O:7])CCC1=O.C[C:10]1[C:15]2[O:16]C3C(=NC=2[C:13]([C:63]([NH:65][C@@H]2C(=O)N[C@H](C(C)C)C(=O)N4[C@@H](CCC4)C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]2C)=O)=[CH:12][CH:11]=1)C(C(N[C@@H]1C(=O)N[C@H](C(C)C)C(=O)N2[C@@H](CCC2)C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]1C)=O)=C(N)C(=O)C=3C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1>[CH2:12]([CH2:13][CH2:63][NH2:65])[CH2:11][CH2:10][C:15]([OH:7])=[O:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 457193Actinomycin D

Product 1

HCID 5646-Aminohexanoic Acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Bromination with N-bromosuccinimide (NBS) is accomplished by adding 2.24 mmoles of actinomycin D in chlorobenzene to 2 mmoles of NBS and a trace of dibenzoyl peroxide. The mixture is heated to 80° C. and allowed to react for 6 hours. The yield of AMD--CH2Br is 70-80%. The brominated derivative is then reacted further with aminocaprioic acid to yield an AMD-aminocaproic acid complex (AMD--CH2NH (CH2)5COOH).

Workup

  1. customto react for 6 hours
  2. customThe brominated derivative is then reacted further with aminocaprioic acid

Sources & evidence

ORD record
ord-df38a86a642f4dd8a884cf46d0df63d0
Source dataset
uspto-grants-1992_10
Patent number
US05155210

Reaction notes

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