Trifluoroacetic acid → 9H-fluoren-9-ylmethyl {6-[(2-{[4-(aminomethyl)phenyl]amino}-2-oxoethyl)amino]-6-oxohexyl}carbamate trifluoroacetate salt

HRID 1755204Notes

Reaction equation

HRID 1755204 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:45])[CH2:18][NH:19][C:20](=[O:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:43])[O:28][CH2:29][CH:30]2[C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:36]3[C:31]2=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:12][CH:11]=1)=O)(C)(C)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>C(Cl)Cl>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[NH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:45])[CH2:18][NH:19][C:20](=[O:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:43])[O:28][CH2:29][CH:30]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=3[C:37]3[C:42]2=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867184039H-fluoren-9-ylmethyl [6-({2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)amino]-2-oxoethyl}amino)-6-oxohexyl]carbamate

Product 1

HCID 1317336739H-fluoren-9-ylmethyl {6-[(2-{[4-(aminomethyl)phenyl]amino}-2-oxoethyl)amino]-6-oxohexyl}carbamate trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of #B120 (1 g, 1.63 mmol, 1.0 eq) in dry DCM (20 mL) at 0° C. was added trifluoroacetic acid (6 mL, large excess). The mixture was stirred at room temperature for 2 hrs and concentrated in vacuo. The residue was suspended in water (30 mL) and lyophilized to afford #B121 (1.2 g, 100%) as a slight yellow solid. 1H NMR (400 Hz, DMSO-d6): δ10.08 (s, 1H), 8.15 (br, 4H), 7.90 (d, 2H), 7.69 (d, 2H), 7.63 (d, 2H), 7.41 (m, 8H), 4.30 (m, 3H), 3.98 (m, 3H), 3.87 (d, 2H), 2.97 (m, 2H), 2.17 (m, 2H), 1.51 (m, 2H), 1.40 (m, 2H), 1.26 (m, 2H): LCMS (Protocol I): m/z 537.1 (M+Na]+, retention time=1.10 minutes.

Workup

  1. concentrationconcentrated in vacuo
  2. customto afford #B121 (1.2 g, 100%) as a slight yellow solid

Sources & evidence

ORD record
ord-e3d49bff711d4b2ab91d6542735e7217
Source dataset
uspto-grants-2015_10
Patent number
US09169264B2

Reaction notes

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