P-Phenylenediamine → (9H-Fluoren-9-yl)methyl (4-aminophenyl)carbamate

HRID 650879Notes

Reaction equation

HRID 650879 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:24](ON3C(=O)CCC3=O)=[O:25])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>O1CCOCC1.O>[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:24]([NH:7][C:6]3[CH:5]=[CH:4][C:3]([NH2:8])=[CH:2][CH:1]=3)=[O:25])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 11450338(9H-Fluoren-9-yl)methyl (4-aminophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

4-((9-Fluorenylmethyloxycarbonyl)amino)aniline is prepared from p-phenylenediamine (2.16 g, 0.02 mole) and N-(9-fluorenylmethoxycarbonyloxy)succinimide (6.75 g, 0.02 mole) in dioxane-water (1:1). Purification is achieved by crystallization. This product is coupled to BOC-L-Glu-α-O-Benzyl using HOBT/DCC. After the usual work-up, the fully-protected amino acid derivative is dissolved in MeOH and treated with hydrogen gas at 1 atmosphere pressure in the presence of palladium-on-carbon catalyst until hydrogen consumption is complete (about 2 hours). Following the usual workup, the starting material:

Workup

  1. customPurification
  2. customis achieved by crystallization
  3. dissolutionAfter the usual work-up, the fully-protected amino acid derivative is dissolved in MeOH
  4. additiontreated with hydrogen gas at 1 atmosphere pressure in the presence of palladium-on-carbon catalyst until hydrogen consumption
  5. custom(about 2 hours)

Sources & evidence

ORD record
ord-1884258bde6045c294b3000145505d0d
Source dataset
uspto-grants-2001_08
Patent number
US06277818B1

Reaction notes

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