Trifluoroacetic acid → HCID 18702171, compound

HRID 356801Notes

Reaction equation

HRID 356801 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[C:28]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1)=[O:13])=O)(C)(C)C.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].C1(OC)C=CC=CC=1>ClCCl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[C:16]1([CH2:15][O:14][C:12]([NH:11][CH2:10][CH2:9][NH2:8])=[O:13])[C:28]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 21480554HCID 21480554, compound

Product 1

HCID 18702171HCID 18702171, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-butyloxycarbonyl-N'-fluorenylmethyloxycarbonylethylene-diamine (20.0 g, 0.052 mol) was treated with trifluoroacetic acid and anisole in dichloromethane (10:10:1) for 1 hour at room temperatute. After evaporation to dryness the crude product was crystallized from solvent mixture of ethyl acetate-n-hexane. Yield 15.0 g (73%). NMR (300 MHz, DMSO-d6, 25° C.) d: 2.85 (m, 2H, CaH2), 3.22 (m, 2H, CbH2), 4.23-4.36 (m, 3H, Fmoc OCH2CH--), 7.37 (m, 1H, NH), 7.34-7.89 (m, 8H, Fmoc), 7.77 (br, 2H, NH2). M.p. 128°-129° C.

Workup

  1. customAfter evaporation to dryness the crude product
  2. customwas crystallized from solvent mixture of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-0ee487c678bd4dc78a5e8790b03d324e
Source dataset
uspto-grants-1998_11
Patent number
US05840485

Reaction notes

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