HCID 145847175, compound → HCID 135854342, compound

HRID 1264199Notes

Reaction equation

HRID 1264199 reaction equation
C(OC([NH:8][CH2:9][C:10]([C:13]1[CH:49]=[CH:48][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27](C(OC(C)(C)C)=O)[CH:26]=[C:25]3[C:38](=[NH:47])[NH:39]C(OC(C)(C)C)=O)=[O:18])=[CH:15][CH:14]=1)([CH3:12])[CH3:11])=O)(C)(C)C>C(Cl)Cl>[NH2:8][CH2:9][C:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[C:25]3[C:38](=[NH:39])[NH2:47])=[O:18])=[CH:48][CH:49]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 145847175HCID 145847175, compound

Product 1

HCID 135854342HCID 135854342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-[tert-Butoxycarbonylamino]-1,1-dimethylethyl)-N-(2-[1-tert-butoxycarbonyl-3-tert-butoxycarbonylcarbamimidoylindol-5-yl]ethyl)benzamide (0.092 g, 0.14 mmol, reference example 1aaal) in CH2Cl2 (8 mL) is added distilled water (0.1 mL) and trifluoroacetic acid (2 mL). After stirring six hours, the reaction mixture is concentrated and then placed under high vacuum to give a quantitative yield of the title compound as a white solid (m.p. 67-70° C). 1H NMR (D2O): δ 1.29 (6H, s), 2.91 (2H, t, J=7 Hz), 3.12 (2H, s), 3.53 (2H, t, J=7 Hz), 7.14 (1H, d, J=8 Hz), 7.36-7.46 (5H, m), 7.54 (1H, s), 7.93 (1H, s). MS (FAB) m/z 378 (M+H)+. Anal. calcd. for C22H27N5O.3C2HO2F3: C, 46.7; H, 4.2; N, 9.7. Found: C, 46.8; H, 4.5; N, 9.8.

Workup

  1. distillationdistilled water (0.1 mL) and trifluoroacetic acid (2 mL)
  2. concentrationthe reaction mixture is concentrated

Sources & evidence

ORD record
ord-25262cd9bd44492b9c0dea4e1e42d927
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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